N-Benzyloxycarbonyl-3-(4-acetoxy-4-phenylpiperidin-1-yl)propylamine → 3-(4-Acetoxy-4-phenylpiperidin-1-yl)propylamine

HRID 1275233Notes

Reaction equation

HRID 1275233 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][C:18]([O:27][C:28](=[O:30])[CH3:29])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)C1C=CC=CC=1>N.CO.[Pd]>[C:28]([O:27][C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][CH2:12][NH2:11])[CH2:20][CH2:19]1)(=[O:30])[CH3:29]

Participants

5

Reactant 1

HCID 22993462N-Benzyloxycarbonyl-3-(4-acetoxy-4-phenylpiperidin-1-yl)propylamine

Product 1

HCID 107788523-(4-Acetoxy-4-phenylpiperidin-1-yl)propylamineYield 99.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A mixture of N-benzyloxycarbonyl-3-(4-acetoxy-4-phenylpiperidin-1-yl)propylamine (3.0 g, 7.3 mmol) and 10% Pd-C (0.3 g) in 1M ammonia in methanol(50 mL) was hydrogenated at 70 psi at room temperature for 4 h. The catalyst was removed by filtration and the solvent was evaporated to leave the product as a viscous oil (2.01 g, 99%), the 1H-NMR showed it to be very pure and was used in the next step without any purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1662d06c2ece48718c3f2d02a5ba54b8
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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