N-(1-Benzyl-piperidin-3-yl)-N-phenyl-propionamide → N-phenyl-N-piperidin-3-yl-propionamide

HRID 1246927Notes

Reaction equation

HRID 1246927 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[C:19]1([N:14]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)[C:15](=[O:18])[CH2:16][CH3:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 12741868N-(1-Benzyl-piperidin-3-yl)-N-phenyl-propionamide

Product 1

HCID 12741869N-phenyl-N-piperidin-3-yl-propionamideYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(1-benzyl-piperidin-3-yl)-N-phenyl-propionamide (165) (150 mg) and Pd—C(10%, 50 mg) and MeOH (50 ml) was stirred under H2 (1 atm) for 24 hr. The catalyst was removed by filtration through Celite to give 166 as a colorless oil (105 mg, 97%). 1H-NMR (300 MHz, CDCl3) δ 7.41 (m, 3H), 7.10 (m, 2H), 3.20 (m 1H), 2.90 (m, 1H), 2.40–2.20 (m, 2H), 1.90 (m, 2H), 1.60 (m, 4H), 1.20 (m, 1H), 1.00 (t, 3H) ppm; LRMS (calculated for C14H21N2O) (M+1)+ 233. found 233.

Workup

  1. customThe catalyst was removed by filtration through Celite

Sources & evidence

ORD record
ord-06f94b1807d84efb91598db626ad20a9
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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