Product Name

  • Name

    3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one

  • EINECS 1308068-626-2
  • CAS No. 545445-44-1
  • Article Data21
  • CAS DataBase
  • Density 1.267 g/cm3
  • Solubility
  • Melting Point
  • Formula C20H25N3O3
  • Boiling Point 624.979 °C at 760 mmHg
  • Molecular Weight 355.437
  • Flash Point 331.775 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 545445-44-1 (3-Morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one)
  • Hazard Symbols
  • Synonyms 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one;
  • PSA 53.09000
  • LogP 2.22420

Synthetic route

morpholine
110-91-8

morpholine

1-(piperidin-2-one-1-yl)-4-(5,6-dihydro-3-chloropyridine-2(1H)-one-1-yl)benzene

1-(piperidin-2-one-1-yl)-4-(5,6-dihydro-3-chloropyridine-2(1H)-one-1-yl)benzene

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Stage #1: 1-(piperidin-2-one-1-yl)-4-(5,6-dihydro-3-chloropyridine-2(1H)-one-1-yl)benzene With bromine; sodium hydroxide In dichloromethane; water at 25 - 35℃; for 4h;
Stage #2: morpholine With triethylamine In N,N-dimethyl-formamide at 95 - 100℃; for 5h; Reagent/catalyst; Solvent; Temperature;		95.2%
5-Chlorovaleroyl chloride
1575-61-7

5-Chlorovaleroyl chloride

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
1267610-26-3

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Stage #1: 5-Chlorovaleroyl chloride; 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 0 - 5℃; for 1h;
Stage #2: With potassium hydroxide In dichloromethane; water at 20℃; Reagent/catalyst; Solvent; Temperature;		94.27%
Stage #1: 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With tetraethylammonium hydroxide In 1,2-dichloro-ethane at 0℃; for 0.166667h;
Stage #2: 5-Chlorovaleroyl chloride In 1,2-dichloro-ethane at 0 - 85℃; for 5h; Solvent; Temperature; Reagent/catalyst;		89%
Stage #1: 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With sodium hydroxide In acetonitrile at 0℃; for 0.166667h; Green chemistry;
Stage #2: 5-Chlorovaleroyl chloride In acetonitrile at 0 - 30℃; for 5h; Reagent/catalyst; Solvent; Temperature; Green chemistry;		87.5%
piperidin-2-one
675-20-7

piperidin-2-one

1-(4-chlorophenyl)-3-morpholine-5,6-dihydropyridine-2(1H)-one

1-(4-chlorophenyl)-3-morpholine-5,6-dihydropyridine-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium hydride In dimethyl sulfoxide at 20℃; for 2h; Solvent;93.1%
With copper(l) iodide; potassium tert-butylate In N,N-dimethyl-formamide at 150℃; for 16h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;76%
3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
545445-40-7

3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one

(2-oxopiperidine-1-yl)chlorobenzene

(2-oxopiperidine-1-yl)chlorobenzene

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate In dimethyl sulfoxide at 20℃; for 6h; Reagent/catalyst; Inert atmosphere;93%
1-(2-oxopiperidin-1-yl)-4-iodobenzene
385425-15-0

1-(2-oxopiperidin-1-yl)-4-iodobenzene

3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
545445-40-7

3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h; Inert atmosphere;86%
5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide

5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 10 - 25℃; Inert atmosphere;84.5%
With potassium tert-butylate In tetrahydrofuran at 5 - 50℃; for 8.5h; Inert atmosphere;3.02 g
1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
473927-69-4

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one

piperidin-2-one
675-20-7

piperidin-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With bromotris(triphenylphosphine)copper(I) In 5,5-dimethyl-1,3-cyclohexadiene Dean-Stark; Reflux;84%
With potassium phosphate; bromotris(triphenylphosphine)copper(I) In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Dean-Stark;84%
Stage #1: 1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one; piperidin-2-one In o-xylene at 25 - 30℃; for 0.166667h;
Stage #2: With copper(l) iodide; potassium carbonate In o-xylene at 140 - 145℃; for 6h;		35 g
5-bromovaleroyl chloride
4509-90-4

5-bromovaleroyl chloride

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
1267610-26-3

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Stage #1: 5-bromovaleroyl chloride; 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 40℃; for 1h;
Stage #2: With sodium hydride In ethyl acetate; tert-butyl alcohol at 10 - 40℃; for 3h; Solvent;		76%
1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one
473927-69-4

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one

piperidin-2-one
675-20-7

piperidin-2-one

Cu(PPh3)3Br

Cu(PPh3)3Br

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With ammonium hydroxide; caesium carbonate In ethyl acetate; toluene
...Expand
1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one
1267610-26-3

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
2: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
4-nitro-aniline
100-01-6

4-nitro-aniline

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: triethylamine / tetrahydrofuran / 5 h / 5 - 20 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 2.5 h / 5 - 20 °C / Inert atmosphere
3: phosphorus pentachloride / chloroform / Reflux
4: 1 h / Reflux
5: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
6: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
7: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5 - 25 °C / Inert atmosphere
2: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
3: phosphorus pentachloride / dichloromethane / 40 °C / Cooling with ice; Inert atmosphere
4: 2 h / 120 °C / Inert atmosphere
5: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
6: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
7: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
5-Chlorovaleroyl chloride
1575-61-7

5-Chlorovaleroyl chloride

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: triethylamine / tetrahydrofuran / 5 h / 5 - 20 °C / Inert atmosphere
2: potassium tert-butylate / tetrahydrofuran / 2.5 h / 5 - 20 °C / Inert atmosphere
3: phosphorus pentachloride / chloroform / Reflux
4: 1 h / Reflux
5: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
6: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
7: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5 - 25 °C / Inert atmosphere
2: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
3: phosphorus pentachloride / dichloromethane / 40 °C / Cooling with ice; Inert atmosphere
4: 2 h / 120 °C / Inert atmosphere
5: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
6: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
7: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / tetrahydrofuran
2.1: sodium t-butanolate / tetrahydrofuran / 4 h / 0 - 40 °C
3.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
4.1: phosphorus pentachloride / Cooling with ice
4.2: 2 h / Reflux
5.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
6.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
6.2: 3 h / 10 - 40 °C
View Scheme
5-chloro-N-(4-nitrophenyl)pentanamide
1039914-85-6

5-chloro-N-(4-nitrophenyl)pentanamide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 5 - 20 °C / Inert atmosphere
2: phosphorus pentachloride / chloroform / Reflux
3: 1 h / Reflux
4: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
5: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
6: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
2: phosphorus pentachloride / dichloromethane / 40 °C / Cooling with ice; Inert atmosphere
3: 2 h / 120 °C / Inert atmosphere
4: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
6: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: tetrabutylammomium bromide; potassium hydroxide / water; tetrahydrofuran / 0 - 20 °C
2.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
3.1: N,N-dimethyl-formamide / 1 h / Reflux
4.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
5.2: 20 °C
View Scheme
1-(4-nitrophenyl)piperidine-2-one
38560-30-4

1-(4-nitrophenyl)piperidine-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: phosphorus pentachloride / chloroform / Reflux
2: 1 h / Reflux
3: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
4: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
5: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: phosphorus pentachloride / dichloromethane / 40 °C / Cooling with ice; Inert atmosphere
2: 2 h / 120 °C / Inert atmosphere
3: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
5: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: phosphorus pentachloride / Cooling with ice
1.2: 2 h / Reflux
2.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 40 °C
3.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1.1: phosphorus pentachloride / Cooling with ice
1.2: 2 h / Reflux
2.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
3.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
2.1: N,N-dimethyl-formamide / 1 h / Reflux
3.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
4.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
4.2: 20 °C
View Scheme
C11H11ClN2O3

C11H11ClN2O3

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1 h / Reflux
2: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
3: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
4: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
503615-03-0

3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C
2: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere
3: potassium tert-butylate / tetrahydrofuran / 8.5 h / 5 - 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
3: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
2.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
2.2: 3 h / 10 - 40 °C
View Scheme
5-bromopentanoic acid
2067-33-6

5-bromopentanoic acid

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 40 - 45 °C
1.2: 2 h / 0 - 30 °C / Inert atmosphere
2.1: sodium t-butanolate / toluene / 2 h / 0 - 5 °C
3.1: phosphorus pentachloride / dichloromethane / 4 h / 25 - 40 °C
4.1: sodium chloride; lithium carbonate / N,N-dimethyl-formamide / 6 h / 25 - 120 °C
5.1: toluene / 8 h / 30 - 120 °C
6.1: o-xylene / 0.17 h / 25 - 30 °C
6.2: 6 h / 140 - 145 °C
View Scheme
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 40 - 45 °C
1.2: 2 h / 0 - 30 °C / Inert atmosphere
2.1: sodium t-butanolate / toluene / 2 h / 0 - 5 °C
3.1: phosphorus pentachloride / dichloromethane / 4 h / 25 - 40 °C
4.1: sodium chloride; lithium carbonate / N,N-dimethyl-formamide / 6 h / 25 - 120 °C
5.1: toluene / 8 h / 30 - 120 °C
6.1: o-xylene / 0.17 h / 25 - 30 °C
6.2: 6 h / 140 - 145 °C
View Scheme
Multi-step reaction with 5 steps
1: triethylamine; dmap / ethyl acetate / 5 - 15 °C
2: potassium phosphate / N,N-dimethyl-formamide; toluene / 7 h / 110 °C
3: phosphorus pentachloride / dichloromethane / Reflux
4: N,N-dimethyl-formamide / 105 - 110 °C
5: bromotris(triphenylphosphine)copper(I) / 5,5-dimethyl-1,3-cyclohexadiene / Dean-Stark; Reflux
View Scheme
Multi-step reaction with 5 steps
1: triethylamine; dmap / ethyl acetate / 5 - 15 °C
2: potassium phosphate / toluene; N,N-dimethyl-formamide / 7 h / 110 °C
3: phosphorus pentachloride / dichloromethane / Reflux
4: N,N-dimethyl-formamide / 105 - 110 °C
5: bromotris(triphenylphosphine)copper(I); potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark
View Scheme
5-bromo-pentanoic acid-(4-iodophenyl)amide

5-bromo-pentanoic acid-(4-iodophenyl)amide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium t-butanolate / toluene / 2 h / 0 - 5 °C
2.1: phosphorus pentachloride / dichloromethane / 4 h / 25 - 40 °C
3.1: sodium chloride; lithium carbonate / N,N-dimethyl-formamide / 6 h / 25 - 120 °C
4.1: toluene / 8 h / 30 - 120 °C
5.1: o-xylene / 0.17 h / 25 - 30 °C
5.2: 6 h / 140 - 145 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium phosphate / N,N-dimethyl-formamide; toluene / 7 h / 110 °C
2: phosphorus pentachloride / dichloromethane / Reflux
3: N,N-dimethyl-formamide / 105 - 110 °C
4: bromotris(triphenylphosphine)copper(I) / 5,5-dimethyl-1,3-cyclohexadiene / Dean-Stark; Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium phosphate / toluene; N,N-dimethyl-formamide / 7 h / 110 °C
2: phosphorus pentachloride / dichloromethane / Reflux
3: N,N-dimethyl-formamide / 105 - 110 °C
4: bromotris(triphenylphosphine)copper(I); potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark
View Scheme
1-(2-oxopiperidin-1-yl)-4-iodobenzene
385425-15-0

1-(2-oxopiperidin-1-yl)-4-iodobenzene

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: phosphorus pentachloride / dichloromethane / 4 h / 25 - 40 °C
2.1: sodium chloride; lithium carbonate / N,N-dimethyl-formamide / 6 h / 25 - 120 °C
3.1: toluene / 8 h / 30 - 120 °C
4.1: o-xylene / 0.17 h / 25 - 30 °C
4.2: 6 h / 140 - 145 °C
View Scheme
Multi-step reaction with 3 steps
1: phosphorus pentachloride / dichloromethane / Reflux
2: N,N-dimethyl-formamide / 105 - 110 °C
3: bromotris(triphenylphosphine)copper(I) / 5,5-dimethyl-1,3-cyclohexadiene / Dean-Stark; Reflux
View Scheme
Multi-step reaction with 3 steps
1: phosphorus pentachloride / dichloromethane / Reflux
2: N,N-dimethyl-formamide / 105 - 110 °C
3: bromotris(triphenylphosphine)copper(I); potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark
View Scheme
3,3-dichloro-1-(4-iodo-phenyl)piperidin-2-one
545445-10-1

3,3-dichloro-1-(4-iodo-phenyl)piperidin-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium chloride; lithium carbonate / N,N-dimethyl-formamide / 6 h / 25 - 120 °C
2.1: toluene / 8 h / 30 - 120 °C
3.1: o-xylene / 0.17 h / 25 - 30 °C
3.2: 6 h / 140 - 145 °C
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 105 - 110 °C
2: bromotris(triphenylphosphine)copper(I) / 5,5-dimethyl-1,3-cyclohexadiene / Dean-Stark; Reflux
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 105 - 110 °C
2: bromotris(triphenylphosphine)copper(I); potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark
View Scheme
3-chloro-1-(4-iodophenyl)-5,6-dihydropyridin-2(1H)-one

3-chloro-1-(4-iodophenyl)-5,6-dihydropyridin-2(1H)-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 8 h / 30 - 120 °C
2.1: o-xylene / 0.17 h / 25 - 30 °C
2.2: 6 h / 140 - 145 °C
View Scheme
3,3-dichloro-1-(4-nitrophenyl)piperidine-2-one
881386-01-2

3,3-dichloro-1-(4-nitrophenyl)piperidine-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2 h / 120 °C / Inert atmosphere
2: water; sodium sulfide / ethanol / 50 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
4: sodium hydride / tetrahydrofuran / 10 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide / 1 h / Reflux
2.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
3.2: 20 °C
View Scheme
5-chloro-pentanoic acid phenylamide
91131-23-6

5-chloro-pentanoic acid phenylamide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium t-butanolate / tetrahydrofuran / 4 h / 0 - 40 °C
2.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
3.1: phosphorus pentachloride / Cooling with ice
3.2: 2 h / Reflux
4.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 40 °C
5.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium t-butanolate / tetrahydrofuran / 4 h / 0 - 40 °C
2.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
3.1: phosphorus pentachloride / Cooling with ice
3.2: 2 h / Reflux
4.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
5.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium hydroxide / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
2.1: nitric acid; sulfuric acid / 0 - 5 °C
3.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
4.1: N,N-dimethyl-formamide / 1 h / Reflux
5.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
6.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
6.2: 20 °C
View Scheme
aniline
62-53-3

aniline

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / tetrahydrofuran
2.1: sodium t-butanolate / tetrahydrofuran / 4 h / 0 - 40 °C
3.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
4.1: phosphorus pentachloride / Cooling with ice
4.2: 2 h / Reflux
5.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
6.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
6.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / tetrahydrofuran
2.1: sodium t-butanolate / tetrahydrofuran / 4 h / 0 - 40 °C
3.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
4.1: phosphorus pentachloride / Cooling with ice
4.2: 2 h / Reflux
5.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
6.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 40 °C
6.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
1.2: 20 °C
2.1: nitric acid; sulfuric acid / 0 - 5 °C
3.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
4.1: N,N-dimethyl-formamide / 1 h / Reflux
5.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
6.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
6.2: 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 25 - 30 °C
2.1: potassium hydroxide / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
3.1: nitric acid; sulfuric acid / 0 - 5 °C
4.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
5.1: N,N-dimethyl-formamide / 1 h / Reflux
6.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
7.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
7.2: 20 °C
View Scheme
1-phenylpiperidin-2-one
4789-09-7

1-phenylpiperidin-2-one

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
2.1: phosphorus pentachloride / Cooling with ice
2.2: 2 h / Reflux
3.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 40 °C
4.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid; nitric acid / 2 h / -5 - 40 °C
2.1: phosphorus pentachloride / Cooling with ice
2.2: 2 h / Reflux
3.1: sodiumsulfide nonahydrate / ethanol / 1 h / 60 °C
4.1: triethylamine / tetrahydrofuran / 1 h / 0 - 40 °C
4.2: 3 h / 10 - 40 °C
View Scheme
Multi-step reaction with 5 steps
1.1: nitric acid; sulfuric acid / 0 - 5 °C
2.1: phosphorus pentachloride / toluene / 1 h / 25 - 80 °C
3.1: N,N-dimethyl-formamide / 1 h / Reflux
4.1: hydrazine hydrate / water; ethanol / 0.5 h / 60 - 65 °C
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 1 h / 0 - 5 °C
5.2: 20 °C
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / tetrahydrofuran / -5 - 20 °C
1.2: 80 °C
2.1: palladium diacetate; caesium carbonate / dimethyl sulfoxide / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: triethylamine / tetrahydrofuran / 1 h / 0 °C
2: sodium hydroxide / dichloromethane / 2 h / 20 °C
3: phosphorus pentachloride / acetonitrile / 2 h / Reflux
4: acetonitrile / 2 h / Reflux
5: bis-triphenylphosphine-palladium(II) chloride; sodium hydride / dimethyl sulfoxide / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: acetic acid / 8 h / 50 °C
2.1: thionyl chloride / dichloromethane / 2 h / 10 - 20 °C
2.2: 2.5 h / 20 °C
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 °C
4.1: sodium t-butanolate / tert-butyl alcohol / 3 h / 85 °C
5.1: copper(l) iodide; potassium tert-butylate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere
View Scheme
5-bromovaleroyl chloride
4509-90-4

5-bromovaleroyl chloride

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / tetrahydrofuran / -5 - 20 °C
1.2: 80 °C
2.1: palladium diacetate; caesium carbonate / dimethyl sulfoxide / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: triethylamine; dmap / ethyl acetate / 5 - 15 °C
2: potassium phosphate / N,N-dimethyl-formamide; toluene / 7 h / 110 °C
3: phosphorus pentachloride / dichloromethane / Reflux
4: N,N-dimethyl-formamide / 105 - 110 °C
5: bromotris(triphenylphosphine)copper(I) / 5,5-dimethyl-1,3-cyclohexadiene / Dean-Stark; Reflux
View Scheme
Multi-step reaction with 5 steps
1: triethylamine; dmap / ethyl acetate / 5 - 15 °C
2: potassium phosphate / toluene; N,N-dimethyl-formamide / 7 h / 110 °C
3: phosphorus pentachloride / dichloromethane / Reflux
4: N,N-dimethyl-formamide / 105 - 110 °C
5: bromotris(triphenylphosphine)copper(I); potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux; Dean-Stark
View Scheme
Multi-step reaction with 5 steps
1: triethylamine / tetrahydrofuran / 1 h / 0 °C
2: sodium hydroxide / dichloromethane / 2 h / 20 °C
3: phosphorus pentachloride / acetonitrile / 2 h / Reflux
4: acetonitrile / 2 h / Reflux
5: bis-triphenylphosphine-palladium(II) chloride; sodium hydride / dimethyl sulfoxide / 2 h / 20 °C
View Scheme
5-bromo-N-{4-[5-(morpholin-4-yl)-6-oxo-3,6-dihydropyridin-1(2H)-yl]phenyl}pentanamide

5-bromo-N-{4-[5-(morpholin-4-yl)-6-oxo-3,6-dihydropyridin-1(2H)-yl]phenyl}pentanamide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
With SPGS-550-M; potassium tert-butylate; potassium iodide In water at 35 - 40℃; Reagent/catalyst; Temperature;
5-chloro-N-(4-chlorophenyl)pentanamide
27471-36-9

5-chloro-N-(4-chlorophenyl)pentanamide

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / dichloromethane / 2 h / 20 °C
2: phosphorus pentachloride / acetonitrile / 2 h / Reflux
3: acetonitrile / 2 h / Reflux
4: bis-triphenylphosphine-palladium(II) chloride; sodium hydride / dimethyl sulfoxide / 2 h / 20 °C
View Scheme
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

ethyl {5-hydroxy-6-oxo-1-[4-(2-oxopiperidin-1-yl)phenyl]-1,2,3,6-tetrahydropyridin-4-yl}(oxo)acetate
1609409-53-1

ethyl {5-hydroxy-6-oxo-1-[4-(2-oxopiperidin-1-yl)phenyl]-1,2,3,6-tetrahydropyridin-4-yl}(oxo)acetate

Conditions
ConditionsYield
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; Ethyl oxalyl chloride With pyridine at 25 - 30℃; for 3h;
Stage #2: With hydrogenchloride; water In ethyl acetate for 1h;		90%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
27143-07-3

ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
503614-91-3

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine; potassium iodide In ethyl acetate for 24h; Reflux;89.9%
With potassium carbonate; carbonic acid dimethyl ester at 82℃; for 0.5h; Temperature; Reagent/catalyst;80.33%
With triethylamine In ethyl acetate; toluene at 85℃; for 7h;76%
With triethylamine; potassium iodide In ethyl acetate at 25 - 80℃; for 24h;54 mg
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate With triethylamine
Stage #2: With hydrogenchloride In water
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

[(4-methoxyphenyl)hydrazino]chloroacetic acid ethyl ester

[(4-methoxyphenyl)hydrazino]chloroacetic acid ethyl ester

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
503614-91-3

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; [(4-methoxyphenyl)hydrazino]chloroacetic acid ethyl ester With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In toluene for 3h; Reflux;
Stage #2: With sulfuric acid In dichloromethane at 20℃; for 3.5h; Reagent/catalyst;		89.6%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

C9H10ClN3O2

C9H10ClN3O2

apixaban

apixaban

Conditions
ConditionsYield
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; C9H10ClN3O2 With triethylamine; potassium iodide In ethyl acetate at 0 - 5℃; for 4h; Reflux;
Stage #2: With hydrogenchloride In water at 20℃; for 1h;		89%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

2-chloro-2-(2-(3-fluoro-4-methoxyphenyl)hydrazono)acetic acid ethyl ester

2-chloro-2-(2-(3-fluoro-4-methoxyphenyl)hydrazono)acetic acid ethyl ester

C27H27FN4O5

C27H27FN4O5

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 80℃; Inert atmosphere;86.2%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate
473927-63-8

ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
503614-91-3

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine; potassium iodide In dichloromethane at 42 - 45℃; Solvent; Temperature;85%
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate With triethylamine; potassium iodide In ethyl acetate for 6h; Reflux;
Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 20℃;		75%
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate With sodium carbonate In acetone at 45 - 50℃; for 3h;
Stage #2: With hydrogenchloride In water at 25 - 30℃; for 2h;		35 g
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate
473927-63-8

ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate

1-(4-methoxy-phenyl)-7a-morpholin-4-yl-7-oxo-6-[4-(2-oxo-piperidin-1-yl)phenyl]-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

1-(4-methoxy-phenyl)-7a-morpholin-4-yl-7-oxo-6-[4-(2-oxo-piperidin-1-yl)phenyl]-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 0℃; Reagent/catalyst; Reflux;80.5%
With triethylamine In ethyl acetate at 0 - 5℃; Reagent/catalyst; Reflux;80%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

ethyl 2-chloro-(4-tolylhydrazono)acetate
27171-88-6, 132815-69-1

ethyl 2-chloro-(4-tolylhydrazono)acetate

C27H28N4O4

C27H28N4O4

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 80℃; Inert atmosphere;79.3%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

3-morpholinyl-1-(4-(2-oxopiperidin-1-yl)phenyl)pyridine-2(1H)-one

3-morpholinyl-1-(4-(2-oxopiperidin-1-yl)phenyl)pyridine-2(1H)-one

Conditions
ConditionsYield
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone With N-Bromosuccinimide In dichloromethane at 20℃; for 3.5h;
Stage #2: With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 4h;		72.4%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 150℃; for 24h; Temperature; Solvent;3.6 g
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

[(2-fluorophenyl)hydrazono]chloroacetic acid ethyl ester
64989-74-8

[(2-fluorophenyl)hydrazono]chloroacetic acid ethyl ester

C26H25FN4O4

C26H25FN4O4

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 80℃; Inert atmosphere;67.9%
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

[(4-methylthio-phenyl)hydrazono]chloroacetic acid ethyl ester

[(4-methylthio-phenyl)hydrazono]chloroacetic acid ethyl ester

C27H28N4O4S

C27H28N4O4S

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 80℃; Inert atmosphere;50.8%
chloro((4-methoxyphenyl)hydrazono]acetic acid ethyl ester

chloro((4-methoxyphenyl)hydrazono]acetic acid ethyl ester

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
503614-91-3

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In ethyl acetate
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

Na-Oxalsaeure-ethylester
74381-54-7

Na-Oxalsaeure-ethylester

{5-hydroxy-6-oxo-1-[4-(2-oxopiperidin-1-yl)phenyl]-1,2,3,6-tetrahydropyridin-4-yl}(oxo)acetic acid
1609409-54-2

{5-hydroxy-6-oxo-1-[4-(2-oxopiperidin-1-yl)phenyl]-1,2,3,6-tetrahydropyridin-4-yl}(oxo)acetic acid

Conditions
ConditionsYield
Stage #1: 5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone; Na-Oxalsaeure-ethylester In ethanol
Stage #2: With hydrogenchloride; water for 1h;
5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone
545445-44-1

5,6‑dihydro‑3‑(4‑morpholinyl)‑1‑[4‑(2‑oxo‑1‑piperidinyl)phenyl]‑2(1H)‑pyridone

apixaban

apixaban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / 3 h / 25 - 30 °C
1.2: 1 h
2.1: isopropyl alcohol; water / 50 - 55 °C
3.1: ammonia / ethylene glycol / 1.5 h / 115 - 120 °C / Autoclave
View Scheme
Multi-step reaction with 4 steps
1.1: ethanol
1.2: 1 h
2.1: hydrogenchloride / Reflux
3.1: isopropyl alcohol; water / 50 - 55 °C
4.1: ammonia / ethylene glycol / 1.5 h / 115 - 120 °C / Autoclave
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / ethyl acetate / 0 °C / Reflux
2: hydrogenchloride / isopropyl alcohol; water / 0 - 5 °C
3: formamide; sodium methylate / N,N-dimethyl-formamide / 0 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / ethyl acetate / 0 - 5 °C / Reflux
2: hydrogenchloride / isopropyl alcohol; water / 0 - 5 °C
3: sodium methylate; formamide / N,N-dimethyl-formamide / 0 - 30 °C
View Scheme

5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone Specification

The 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone, with the CAS registry number 545445-44-1, is also known as 3-Morpholin-4-yl-1-[4-(2-oxopiperidin-1-yl)phenyl]-5,6-dihydro-1H-pyridin-2-one. This chemical's molecular formula is C20H25N3O3 and molecular weight is 355.00. What's more, its systematic name is called 3-(4-Morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-5,6-dihydro-2(1H)-pyridinone.

Physical properties about 5,6-Dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-1-piperidinyl)phenyl]-2(1H)-pyridinone are: (1)ACD/LogP: 1.668; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.67; (4)ACD/LogD (pH 7.4): 1.67; (5)ACD/BCF (pH 5.5): 10.89; (6)ACD/BCF (pH 7.4): 10.91; (7)ACD/KOC (pH 5.5): 192.12; (8)ACD/KOC (pH 7.4): 192.56; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 53.09 Å2; (13)Index of Refraction: 1.611; (14)Molar Refractivity: 97.409 cm3; (15)Molar Volume: 280.46 cm3; (16)Polarizability: 38.616×10-24cm3; (17)Surface Tension: 56.20 dyne/cm; (18)Density: 1.267 g/cm3; (19)Flash Point: 331.775 °C; (20)Enthalpy of Vaporization: 92.538 kJ/mol; (21)Boiling Point: 624.979 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1CCCCN1c2ccc(cc2)N3CC\C=C(/C3=O)N4CCOCC4
(2) InChI: InChI=1S/C20H25N3O3/c24-19-5-1-2-10-22(19)16-6-8-17(9-7-16)23-11-3-4-18(20(23)25)21-12-14-26-15-13-21/h4,6-9H,1-3,5,10-15H2
(3) InChIKey: SCVWQFDPLBFZAP-UHFFFAOYSA-N

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