1-Benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine → 4-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

Participants

Reaction Steps

A mixture of 1-benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine (12.3 g, 32.4 mmol), ethanol (150 mL), and 10% palladium on carbon (1.4 g) was hydrogenated in a Parr apparatus (initial hydrogen pressure was 48 psi). After 2.5 hours, the mixture was filtered through celite and concentrated. The residue was triturated with ether/hexane to obtain 4.98 g (63%) of 4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine as a white solid which had mp 130.5°-132° C. Analysis calculated for C12 H14F3NO--0.25 H2O: C, 57.71; H, 5.85; N, 5.61. Found: C, 57.91; H 5.77; N, 5.54.

Provenance & Evidence