Benzenepropanoic acid → N-[1-(4-methoxy-phenyl)-piperidin-4-yl]-3-phenyl-propionamide

HRID 634781Notes

Reaction equation

HRID 634781 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CN(C=O)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1>O>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([N:37]2[CH2:42][CH2:41][CH:40]([NH:43][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:39][CH2:38]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 246902051-(4-Methoxyphenyl)piperidin-4-amine

Product 1

HCID 21260533N-[1-(4-methoxy-phenyl)-piperidin-4-yl]-3-phenyl-propionamideYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-phenyl propionic acid (360 mg, 2.4 mmol), CDI (410 mg, 2.5 mmol) and DMF (20 ml) was stirred at 50° for 1 h. After cooling to 0°, 1-(4-methoxy-phenyl)-piperidin-4-ylamine (500 mg, 2.4 mmol) was added and stirring continued for 1 h. After the addition of H2O (60 ml) the white precipitate was collected to give N-[1-(4-methoxy-phenyl)-piperidin-4-yl]-3-phenyl-propionamide (618 mg, 76%, MS: m/e=339.3 (M+H+)).

Workup

  1. temperatureAfter cooling to 0°
  2. stirringstirring
  3. waitcontinued for 1 h
  4. customwas collected

Sources & evidence

ORD record
ord-fdfe3c29db0143799b56a88a8ba25bb0
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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