1-Benzyl-4-hydroxypiperidine-4-carbonitrile → 4-(Aminomethyl)-1-benzylpiperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-benzyl-4-hydroxy-piperidine-4-carbonitrile (5.00 g, 19.78 mmol) and BH3.THF (59.35 mmol, 59.35 mL, 1M in THF) was heated at 80° C. for 1 h. Cooled to 0° C. and quenched with conc. HCl (20 mL), the reaction solution was then stirred at rt in 1 h. The reaction solution was basified with 10N NaOH to pH 8, and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 4-aminomethyl-1-benzyl-piperidin-4-ol.

Provenance & Evidence