HCID 12900709, compound → cis-3-Hydroxy-5-(p-trifluoromethylphenyl)piperidine

HRID 2166567Notes

Reaction equation

HRID 2166567 reaction equation
C([N:8]1[CH2:13][CH:12]([OH:14])[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:14][C@H:12]1[CH2:11][C@@H:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)[CH2:9][NH:8][CH2:13]1

Participants

5

Reactant 2

HCID 12900709HCID 12900709, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86738912cis-3-Hydroxy-5-(p-trifluoromethylphenyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-5-hydroxy-1,2,5,6-tetrahydro-3-(p-trifluoromethylphenyl)pyridine (5.9 g) in methanol (200 ml) was hydrogenated over 10% palladium on carbon (500 mg) in a Parr apparatus at 30 psi (about 2.11×104 kg/sq.m.) and room temperature. After the theoretical uptake of hydrogen had occurred (about 3 hours), the catalyst was removed by filtration and the solvent evaporated under reduced pressure. Recrystallisation of the residue from toluene gave the title compound as the free base (4 g). The free base was dissolved in a small volume of IPA and treated with an excess of etherial hydrogen chloride. On cooling crystals of the title compound hydrochloride separated, m.p. 189°-92°.

Workup

  1. custom(about 3 hours)
  2. customthe catalyst was removed by filtration
  3. customthe solvent evaporated under reduced pressure
  4. customRecrystallisation of the residue from toluene

Sources & evidence

ORD record
ord-b37dde183b654c0d8c93d12242be1743
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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