N-(1-Benzyl-4-phenylpiperidin-4-YL)acetamide → N-(4-Phenylpiperidin-4-yl)acetamide

HRID 1829181Notes

Reaction equation

HRID 1829181 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([NH:20][C:21](=[O:23])[CH3:22])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[C:14]1([C:11]2([NH:20][C:21](=[O:23])[CH3:22])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 18964199N-(1-Benzyl-4-phenylpiperidin-4-YL)acetamide

Product 1

HCID 15886675N-(4-Phenylpiperidin-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(1-Benzyl-4-phenyl-4-piperidinyl)acetamide (Bioorg. Med. Chem. Lett. 1996; 6(19); 2307) (49 g, 158 mmol), and palladium hydroxide (5 g) in methanol (600 ml) was hydrogenated at 50 psi and room temperature for 18 hours. The mixture was filtered, the filtrate concentrated under reduced pressure and the residue azeotroped with dichloromethane to give the title compound as a foam.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe residue azeotroped with dichloromethane

Sources & evidence

ORD record
ord-3f9a95e0015e442391fdeb845217494e
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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