1-Benzyl-4-piperidone → 4-(Aminomethyl)-1-benzylpiperidin-4-ol

Participants

Reaction Steps

To neat 1-benzyl-4-piperidone (2.22 mL, 12 mmol) was added trimethylsilyl cyanide (1.95 mL, ˜15 mmol) and zinc iodide (˜5 mg). The solution was stirred for 6 hours or until reaction was completed as indicated by tlc. This oil was dissolved in diethyl ether (30 mL), filtered to remove some solid and added dropwise to a solution of diethyl ether (15 mL) containing 1M lithium aluminium hydride/diethyl ether (30 mL). After stirring at ambient temp. for 2 hours, the reaction was carefully quenched with aqueous sat'd sodium sulfate. This suspension was diluted with more diethyl ether, filtered to remove solids, and the solvent evaporated under partial vacuum to give the crude title compound as an oil.

Provenance & Evidence