Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylate → 1-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

Participants

Reaction Conditions

Reaction Steps

To a slurry of lithium aluminum hydride (330 mg, 8.7 mmol) in anhydrous diethyl ether (25 mL) at 0° C., a solution of ethyl 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylate (2.8 g, 7.94 mmol) in diethyl ether (10 mL) was added dropwise with the temp. of the reacting mixture maintained below 10° C. The resulting mixture was stirred at 0° C. for 30 min, and quenched with successive addition of water (0.33 mL), 15% aqueous NaOH (0.33 mL), and water (1 mL). The resultant slurry was stirred at room temp. for 30 min., and was filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title alcohol as white solid.

Provenance & Evidence