Benzylamine → 1-(2-Phenylethyl)piperidin-4-amine

Participants

Reaction Steps

Following the procedure of Lobbezoo, J. Med. Chem. 24:777 (1981). N-(β-phenylethyl)-4-piperidinone (15.0 g, 74.0 mmol) dissolved in 200 ml of methanol containing 1 ml of a 4% thiophene in methanol solution is treated with benzyl amine (10.0 g, 93.0 mmol) and 2 g of 10% palladium-on-carbon in a Parr flask and hydrogenated for 18 hours (initial pressure, 26.5 psi, final pressure 22.0 psi). The catalyst is filtered and replaced with 2.0 g of fresh 10% palladium-on-carbon. The catalyst is filtered and replaced again with 4.8 g of fresh 10% palladium-on-carbon. The hydrogenation is followed over 3 days, at which point, hydrogen uptake ceases (initial pressure, 35 psi, final pressure, 29 psi). The catalyst is filtered through Celite and is washed with methanol. GLC analysis (2 ft SE-30, 100 C, 1 minute, programmed 20 C/minute rise to 250 C) indicated that 7% unreacted benzyl amine remained). This material nevertheless was used for subsequent experiments.

Provenance & Evidence