1-(3-Phenyl-propyl)-piperidine-4-carboxylic acid benzyl ester → 1-(3-Phenylpropyl)piperidine-4-carboxylic acid

HRID 1177877Notes

Reaction equation

HRID 1177877 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:20]1([CH2:19][CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([C:9]([OH:10])=[O:8])[CH2:12][CH2:13]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 595595721-(3-Phenyl-propyl)-piperidine-4-carboxylic acid benzyl ester

Product 1

HCID 176040671-(3-Phenylpropyl)piperidine-4-carboxylic acidYield 93.93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (378 mg) was added to a stirred solution of 1-(3-phenyl-propyl)-piperidine-4-carboxylic acid benzyl ester (1.89 g, 5 mmol) in MeOH (38 mL) and stirring was continued under hydrogen atmosphere for 2 hrs. The mixture was filtered over a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to afford 1.502 mg (93.93% yield) of 1-(3-phenyl-propyl)-piperidine-4-carboxylic acid. LCMS Purity: 95.08%.

Workup

  1. filtrationThe mixture was filtered over a bed of celite
  2. washThe celite was washed with MeOH
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3aaae2ddb3634d84adb9c9cdca633efb
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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