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

HRID 266775Notes

Reaction equation

HRID 266775 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-5869eaeb9f964d68a6b0d161ca3ddd8e
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

Loading…