HCID 18187860, compound → HCID 18187489, compound

HRID 278223Notes

Reaction equation

HRID 278223 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([F:27])([F:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[F:27][C:19]([F:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][CH2:17][CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 18187860HCID 18187860, compound

Product 1

HCID 18187489HCID 18187489, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

The partially purified 1-(benzyloxycarbonyl)-4-(3,3-difluoro-3-phenylprop-1-yl)piperidine (247 mg) was hydrogenated at atmospheric pressure in 95% ethanol (4.0 mL) containing 20% Pd(OH)2/C (60 mg). After 6 h, additional 20% Pd(OH)2/C (32 mg) was added and the hydrogenation was continued for another 16 h. The mixture was filtered and the catalyst was washed with 95% ethanol. Evaporation of the filtrate gave 164 mg of crude 4-(3,3-difluoro-3-phenylprop-1-yl)piperidine as a colorless syrup.

Workup

  1. waitthe hydrogenation was continued for another 16 h
  2. filtrationThe mixture was filtered
  3. washthe catalyst was washed with 95% ethanol
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-3a272b0fe6d94067be799d1cc1018fa0
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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