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

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

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°.