Acetic Acid → N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline

HRID 483483Notes

Reaction equation

HRID 483483 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])(=[O:3])[NH2:2].[C:13]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C>C(O)C.O=[Pt]=O>[C:13]([N:21]1[CH2:26][CH2:25][CH:24]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][C:1](=[O:3])[NH2:2])[CH2:23][CH2:22]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 90583N-Benzoyl-4-piperidoneHCID 190312342-Aminobenzenepropanamide

Product 1

HCID 19031102N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

2-(2-Carbamoylethyl)aniline (37 g) and 1-benzoyl-4-oxopiperidine (67.6 g) are dissolved in ethanol (500 ml) and to the solution is added acetic acid to adjust the pH of the solution to about 5.5. To the solution is further added PtO2 (1 g) and the mixture is stirred under 1 atm. at room temperature under H2 atmosphere. When H2 is absorbed up to 5 liters, the reaction is stopped and the catalyst is separated by filtration. The filtrate is concentrated to give N-(1-benzoyl-4-piperidinyl)-2-(2-carbamoylethyl)aniline.

Workup

  1. customWhen H2 is absorbed up to 5 liters
  2. customthe catalyst is separated by filtration
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-a597d6581fb643beb34b8b2696414c64
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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