1-benzyl-4-(1,2,3,4-tetrahydro-2-oxo-3-quinazolinyl)piperidine
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol for 48h; | 100% |
With hydrogen; Pd/C In ethanol at 60℃; under 1500.15 Torr; | 85% |
With hydrogen; palladium on activated charcoal In ethanol at 60℃; under 1500.15 Torr; | 85% |
tert-butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-3-yl)piperidine-1-carboxylate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; | 92% |
2-nitro-benzaldehyde
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: hydrogen / palladium on activated charcoal / ethanol 3: acetonitrile / Reflux View Scheme |
4-amino-1-benzylpiperidine
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: hydrogen / palladium on activated charcoal / ethanol 3: acetonitrile / Reflux View Scheme | |
Multi-step reaction with 5 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 3: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 4: tetrahydrofuran / 5 h / 20 °C 5: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme |
2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine
1,1'-carbonyldiimidazole
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Stage #1: 2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine; 1,1'-carbonyldiimidazole In acetonitrile Reflux; Stage #2: With hydrogen; palladium(II) hydroxide In methanol |
(1-benzyl-piperidin-4-yl)-(2-nitro-benzyl)-amine
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen / palladium on activated charcoal / ethanol 2: acetonitrile / Reflux View Scheme |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 2: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 3: tetrahydrofuran / 5 h / 20 °C 4: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme |
2-amino-N-(1-benzyl-piperidin-4-yl)-benzamide
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 2: tetrahydrofuran / 5 h / 20 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme |
2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 5 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme |
2-(tert-butyloxycarbonylamino)benzoic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C 3: lithium aluminium tetrahydride / 1,4-dioxane / 3 h / Reflux 4: tetrahydrofuran / 5 h / 20 °C 5: hydrogen; palladium 10% on activated carbon / methanol / 48 h View Scheme |
tert-butyl 4-((2-aminobenzyl)amino)piperidine-1-carboxylate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 2: trifluoroacetic acid / dichloromethane / 20 °C View Scheme |
N-tert-butyloxycarbonylpiperidin-4-one
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C 2: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme |
2-amino-1-benzylamine
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C 2: triethylamine / acetonitrile / 18 h / 20 °C / Reflux 3: trifluoroacetic acid / dichloromethane / 20 °C View Scheme |
1,1'-Carbonyl-di-(1,2,4-triazole)
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
2-Amino-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
1,1'-Carbonyl-di-(1,2,4-triazole)
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
1,1'-Carbonyl-di-(1,2,4-triazole)
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
1,1'-Carbonyl-di-(1,2,4-triazole)
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 100% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
(+/-)-4-(3,4-dimethoxyphenyl)-3-methoxycarbonylbutanoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 100% |
β-(methoxycarbonyl)-1-naphthalenebutanoic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 100% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 100% |
1-(methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-nitrophenyl carbonate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
1-(Methoxycarbonyl)-2-(2-((2-(trimethylsilyl)ethoxy)methyl)-7-methyl-2H-indazol-5-yl)ethyl 4-(1,2-dihydro-2-oxoquinazolin-3(4H)-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48h; | 100% |
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 48h; | 100% |
(R)-methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
(R)-methyl-2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamido)-3-(7-methyl-1H-indazol-5-yl)propanoate
Conditions | Yield |
---|---|
Stage #1: methyl (R)-2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate With di(succinimido) carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In N,N-dimethyl-formamide for 24h; | 100% |
3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide | 98% |
3,5-dibromo-4-hydroxy-β-(methoxycarbonyl)-benzenebutanoic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 98% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
(S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (S)-2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-succinic acid 1-methyl ester With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethylformamide) at 20℃; for 1h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethylformamide) at 20℃; Stage #3: With potassium carbonate; citric acid more than 3 stages; | 98% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
3-(4-bromo-3-methyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-carbonyl]-amino}-propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 2-amino-3-(4-bromo-3-methyl-phenyl)-propionic acid ethyl ester hydrochloride With 1,1'-Carbonyl-di-(1,2,4-triazole); triethylamine In DMF (N,N-dimethylformamide) at 0 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethylformamide) at 80℃; for 1.5h; | 97% |
1,1'-Carbonyl-di-(1,2,4-triazole)
2-amino-3-(3,4-diethyl-phenyl)-propionic acid methylester
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-carbonyl]-amino}-propionic acid methylester
Conditions | Yield |
---|---|
Stage #1: 1,1'-Carbonyl-di-(1,2,4-triazole); 2-amino-3-(3,4-diethyl-phenyl)-propionic acid methylester With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 10℃; for 1.5h; Stage #2: In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #3: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one for 10h; Heating / reflux; | 97% |
(5-bromouracil)acetic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
Stage #1: (5-bromouracil)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In N,N-dimethyl-formamide at 20℃; for 18h; | 97% |
(+/-)-2-Amino-3-(7-chloro-1H-indazol-5-yl)-propionic acid methyl ester
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
1,1'-carbonyldiimidazole
(+/-)-3-(7-chloro-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (+/-)-2-Amino-3-(7-chloro-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃; | 94% |
In tetrahydrofuran |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran; N,N-dimethyl-formamide | 93% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 92% |
(+/-)-2-Amino-3-(7-ethyl-1H-indazol-5-yl)-propionic acid methyl ester
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
1,1'-carbonyldiimidazole
(+/-)-3-(7-ethyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (+/-)-2-Amino-3-(7-ethyl-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.333333h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃; | 92% |
In tetrahydrofuran |
1,1'-Carbonyl-di-(1,2,4-triazole)
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 90% |
(R)-2-amino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester
di(succinimido) carbonate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
(R)-2-{[4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (R)-2-amino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-propionic acid methyl ester; di(succinimido) carbonate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.666667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In dichloromethane at 20℃; | 90% |
With N-ethyl-N,N-diisopropylamine In dichloromethane | 1.15 g (90%) |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
2-(4-chloro-3-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-butanoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 2-(4-chloro-3-trifluoromethyl-benzyl)-succinic acid 1-methyl ester With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran; water at 20℃; for 2h; Stage #3: With sodium hydrogencarbonate In water | 89% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
1,1'-carbonyldiimidazole
Conditions | Yield |
---|---|
Stage #1: 1,1'-carbonyldiimidazole; 3,5-dibromo-D-tyrosine methyl ester With 1,2,4-Triazole In DMF (N,N-dimethyl-formamide) at 10 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethyl-formamide) at 50 - 55℃; for 1.5h; | 88% |
Stage #1: 1,1'-carbonyldiimidazole; 3,5-dibromo-D-tyrosine methyl ester With 1,2,4-Triazole In DMF (N,N-dimethyl-formamide) at 10 - 20℃; for 2h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In DMF (N,N-dimethyl-formamide) at 20 - 55℃; for 1.5h; Product distribution / selectivity; | 88% |
With 1,2,4-Triazole In N,N-dimethyl-formamide | 51% |
C15H22N2O2
di(succinimido) carbonate
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
Conditions | Yield |
---|---|
In dichloromethane | 87% |
4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-{2-oxo-2-[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidin-1-yl]-ethyl}-malonic acid diethyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃; for 16h; | 87% |
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
6,7-dimethoxy-4-chloroquinazoline
3-[1-(6,7-Dimethoxy-quinazolin-4-yl)-piperidin-4-yl]-3,4-dihydro-1H-quinazolin-2-one; hydrochloride
Conditions | Yield |
---|---|
In methanol Heating; | 86% |
(+/-)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester
3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one
(+/-)-3-(7-ethyl-3-methyl-1H-indazol-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (+/-)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 0.25h; Stage #2: 3-piperidin-4-yl-3,4-dihydro-1H-quinazoline-2-one In tetrahydrofuran at 20℃; | 86% |
The 3-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one, its cas register number is 79098-75-2. It also can be called as 2(1H)-Quinazolinone,3,4-dihydro-3-(4-piperidinyl)- and the Systematic name about this chemical is 3-piperidin-4-yl-3,4-dihydroquinazolin-2(1H)-one.
Following are the chemical properties about 3-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one: (1)#H bond acceptors: 4; (2)#H bond donors: 2; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 44.37Å2; (5)Index of Refraction: 1.581; (6)Molar Refractivity: 65.311 cm3; (7)Molar Volume: 195.993 cm3; (8)Polarizability: 25.891x10-24cm3; (9)Surface Tension: 45.599 dyne/cm; (10) Enthalpy of Vaporization: 71.942 kJ/mol; (11)Boiling Point: 459.008 °C at 760 mmHg
This chemical can be described computed from structure:
(1)SMILES:O=C2N(Cc1ccccc1N2)C3CCNCC3
(2)InChI: InChI=1/C13H17N3O/c17-13-15-12-4-2-1-3-10(12)9-16(13)11-5-7-14-8-6-11/h1-4,11,14H,5-9H2,(H,15,17)
(3)InChIKey: KSTFHYBYFDYWSD-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C13H17N3O/c17-13-15-12-4-2-1-3-10(12)9-16(13)11-5-7-14-8-6-11/h1-4,11,14H,5-9H2,(H,15,17)
(5)Std. InChIKey: KSTFHYBYFDYWSD-UHFFFAOYSA-N
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