Hydrochloric Acid → 4-Phenylpiperidine-4-methanol

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Reaction Steps

4-Phenyl-piperidine-4-carboxylic acid (1.0 g, 2.7 mmol) was added to a solution of borane in THF (1 M, 15 mL). The mixture was then heated at reflux for 1 hour, and then methanol (3 mL) was carefully added dropwise. The mixture was heated at reflux for 1 hour and allowed to cool to room temperature and hydrochloric acid (1 N, 2 mL) was added and the mixture left to stand overnight. The solvent was then removed by evaporation under vacuum and the residue triturated with acetone. The resulting solid was isolated by filtration, washed with diethyl ether and dried under vacuum to afford the title compound as a white solid (0.37 g). LCMS m/z 192.2 [M+H]+. R.T.=0.69 min (Analytical Method 4).

Provenance & Evidence