3-(S)-Phenylcarbamoyl-piperidine-1-carboxylic acid benzyl ester → N-Phenylpiperidine-3-carboxamide

HRID 720060Notes

Reaction equation

HRID 720060 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](=[O:25])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:19]1([NH:18][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 587375303-(S)-Phenylcarbamoyl-piperidine-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 16227111N-Phenylpiperidine-3-carboxamideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(S)-Phenylcarbamoyl-piperidine-1-carboxylic acid benzyl ester (1.80 mol, 608 mg) and Pd—C 30% (100 mg) in CH3OH (10 mL) at 25° C. were added to a Paar hydrogenator low pressure reaction vessel. The mixture was reacted at 55 psi with vigorous shaking until hydrogen uptake subsided (2 h). The catalyst was filtered through a pad of celite. The filtrate was concentrated in vacuo which provided piperidine-3-carboxylic acid phenylamide (367 mg, 367 mg theoretical, 99%) as a white foam: LRMS m/z 205 (M++1, C12H16N2O requires 205).

Workup

  1. customThe mixture was reacted at 55 psi
  2. custom(2 h)
  3. filtrationThe catalyst was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated in vacuo which

Sources & evidence

ORD record
ord-1a8ff64acd2145aa85ccbaaf1f77f85a
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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