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Synthetic route

piperidin-4-one; hydrochloride sesquiethylate

piperidin-4-one; hydrochloride sesquiethylate

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

Conditions
ConditionsYield
With hydrogenchloride; water
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

phenoxyamine hydrochloride
6092-80-4

phenoxyamine hydrochloride

1,2,3,4-tetrahydro[1]benzofuro[3,2-c]pyridine hydrochloride
49540-52-5

1,2,3,4-tetrahydro[1]benzofuro[3,2-c]pyridine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol100%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4,4-dimethoxypiperidine monohydrochloride
77542-16-6

4,4-dimethoxypiperidine monohydrochloride

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 22h;100%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

trityl chloride
76-83-5

trityl chloride

1-triphenylmethyl-4-piperidone
112257-60-0

1-triphenylmethyl-4-piperidone

Conditions
ConditionsYield
With triethylamine In N-methyl-acetamide; water98.3%
With triethylamine In N,N-dimethyl-formamide at 60℃; for 5h;70.2%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water for 12h; Cooling with ice;94%
With sodium hydroxide In 1,4-dioxane92.5%
With triethylamine In dichloromethane; ethyl acetate86%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium carbonate
497-19-8

sodium carbonate

4-chloro-2-(trifluoromethyl)pyrimidine
1514-96-1

4-chloro-2-(trifluoromethyl)pyrimidine

1-[2-(Trifluoromethyl)-4-pyrimidinyl]-4-piperidone

1-[2-(Trifluoromethyl)-4-pyrimidinyl]-4-piperidone

Conditions
ConditionsYield
In dichloromethane92%
2-(thiophen-2-yl)ethyl methanesulfonate
61380-07-2

2-(thiophen-2-yl)ethyl methanesulfonate

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

N-[2-(2-thienyl)ethyl]-4-piperidinone
92065-14-0

N-[2-(2-thienyl)ethyl]-4-piperidinone

Conditions
ConditionsYield
Stage #1: 4-piperidone monohydrochloride monohydrate With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile at 60℃; for 1h;
Stage #2: 2-(thiophen-2-yl)ethyl methanesulfonate In acetonitrile at 80℃; for 24h; Reagent/catalyst;
90%
7-bromo-1H-indole
51417-51-7

7-bromo-1H-indole

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

7-bromo-3-piperidin-4-yl-1H-indole
312631-09-7

7-bromo-3-piperidin-4-yl-1H-indole

Conditions
ConditionsYield
89%
[1,1,2,2-(2)H4]ethane-1,2-diol
2219-51-4

[1,1,2,2-(2)H4]ethane-1,2-diol

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

2,2,3,3-tetradeutero-1,4-dioxa-8-azaspiro<4,5>decane
84376-17-0

2,2,3,3-tetradeutero-1,4-dioxa-8-azaspiro<4,5>decane

Conditions
ConditionsYield
In benzene for 48h; Heating;88%
C16H15FO2

C16H15FO2

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

1-[2′-(2-fluoroethyl)-2-methylbiphenyl-4-carbonyl]-piperidin-4-one

1-[2′-(2-fluoroethyl)-2-methylbiphenyl-4-carbonyl]-piperidin-4-one

Conditions
ConditionsYield
Stage #1: C16H15FO2 With 4-methyl-morpholine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate In N,N-dimethyl-formamide for 0.166667h; Cooling with ice;
Stage #2: 4-piperidone monohydrochloride monohydrate In N,N-dimethyl-formamide at 0 - 20℃;
88%
1-amino-1,2,3,4-tetrahydroquinoline
5825-45-6

1-amino-1,2,3,4-tetrahydroquinoline

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

5,6,8,9,10,11-hexahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

5,6,8,9,10,11-hexahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline

Conditions
ConditionsYield
With hydrogenchloride85%
1-amino-1,2,3,4-tetrahydroquinoline
5825-45-6

1-amino-1,2,3,4-tetrahydroquinoline

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

5,6,8,9,10,11-hexahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline; hydrochloride

5,6,8,9,10,11-hexahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 3h; Reflux;85%
2-methyl-1,2-pentanediol
20667-05-4

2-methyl-1,2-pentanediol

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

4-piperidone 2-propylpropyleneacetal

4-piperidone 2-propylpropyleneacetal

Conditions
ConditionsYield
With p-toluenesulfonic acid monohydrate In toluene84%
4-fluoro-2-methoxy-1-nitrobenzene
448-19-1

4-fluoro-2-methoxy-1-nitrobenzene

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

1-(3-methoxy-4 nitrophenyl)piperidin-4-one
761440-64-6

1-(3-methoxy-4 nitrophenyl)piperidin-4-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; Inert atmosphere;84%
5-methoxylindole
1006-94-6

5-methoxylindole

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

4-(5-methoxy-1H-indol-3-yl)piperidine
52157-82-1

4-(5-methoxy-1H-indol-3-yl)piperidine

Conditions
ConditionsYield
83%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine
41840-28-2

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 6h; Ambient temperature;81.3%
5-(bromomethyl)-2-(2-nitrophenyl)benzo[d]oxazole

5-(bromomethyl)-2-(2-nitrophenyl)benzo[d]oxazole

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

1-((2-(2-nitrophenyl)benzo[d]oxazol-5-yl)methyl)piperidin-4-one

1-((2-(2-nitrophenyl)benzo[d]oxazol-5-yl)methyl)piperidin-4-one

Conditions
ConditionsYield
With acetic anhydride; potassium carbonate In acetonitrile at 20℃; for 5h;81.2%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

1-chloro-2-(chloromethyl)benzene
611-19-8

1-chloro-2-(chloromethyl)benzene

N-[1-(2-Chlorobenzyl)-4-piperidyl]-N-(1H-5 indazolyl)amine

N-[1-(2-Chlorobenzyl)-4-piperidyl]-N-(1H-5 indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile80%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

N-[1-(4-Fluorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

N-[1-(4-Fluorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile79%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

1-Chloro-3-chloromethyl-benzene
620-20-2

1-Chloro-3-chloromethyl-benzene

N-[1-(3-Chlorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

N-[1-(3-Chlorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate In methanol; acetonitrile79%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

N-[1-(4-Chlorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

N-[1-(4-Chlorobenzyl)-4-piperidyl]-N-(1H-5-indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile79%
6-chloropiperonyl chloride
23468-31-7

6-chloropiperonyl chloride

1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

N-{1-[(6-Chloro-1,3-benzodioxol-5-yl)methyl]-4-piperidyl}-N-(1H-5-indazolyl)amine

N-{1-[(6-Chloro-1,3-benzodioxol-5-yl)methyl]-4-piperidyl}-N-(1H-5-indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile78%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

6-chloro-7H-purine
87-42-3

6-chloro-7H-purine

1-(purin-6-yl)piperidin-4-one

1-(purin-6-yl)piperidin-4-one

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 50℃; for 2h;77%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

N-(1H-5-Indazolyl)-N-[1-(4-methylbenzyl)-4-piperidyl]amine

N-(1H-5-Indazolyl)-N-[1-(4-methylbenzyl)-4-piperidyl]amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile76%
2-bromophenylhydrazine hydrochloride
50709-33-6

2-bromophenylhydrazine hydrochloride

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloric acid salt
1059630-11-3

6-bromo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloric acid salt

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 6h; Reflux; Inert atmosphere;76%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

2,6-dichloro-7H-purine
5451-40-1

2,6-dichloro-7H-purine

1-(2-chloropurin-6-yl)piperidin-4-one

1-(2-chloropurin-6-yl)piperidin-4-one

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 60℃; for 2h;76%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

4-benzyloxybenzyl chloride
836-42-0

4-benzyloxybenzyl chloride

N-{1-[4-(Benzyloxy)benzyl]-4-piperidyl}-N-(1H-5-indazolyl)amine

N-{1-[4-(Benzyloxy)benzyl]-4-piperidyl}-N-(1H-5-indazolyl)amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile75%
1H-indazol-5-ylamine
19335-11-6

1H-indazol-5-ylamine

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

N-(1H-5-Indazolyl)-N-[1-(4-methoxybenzyl)-4-piperidyl]amine

N-(1H-5-Indazolyl)-N-[1-(4-methoxybenzyl)-4-piperidyl]amine

Conditions
ConditionsYield
With potassium carbonate; acetic acid In methanol; acetonitrile74%
2-phenyl-indole
948-65-2

2-phenyl-indole

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole
221109-25-7

2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Conditions
ConditionsYield
With phosphoric acid In acetic acid; ethyl acetate73%
1-amino-2,3-dihydroindole hydrochloride
92259-86-4

1-amino-2,3-dihydroindole hydrochloride

4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

4,5,7,8,9,10-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole
313666-86-3

4,5,7,8,9,10-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;73%
4-piperidone monohydrochloride monohydrate
40064-34-4

4-piperidone monohydrochloride monohydrate

2,4-difluorobenzoyl chloride
72482-64-5

2,4-difluorobenzoyl chloride

4-(2,4-difluorobenzoyl)piperidinone

4-(2,4-difluorobenzoyl)piperidinone

Conditions
ConditionsYield
With triethylamine In dichloromethane71%

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