Hydrochloric Acid → 4-(Diphenylmethyl)piperidine hydrochloride

Participants

Reaction Steps

4-diphenylmethylenepiperidine hydrochloride (6.21 g) was added to methanol (30 ml) and the atmosphere was replaced with argon. To the mixture, 10% palladium-carbon (1.54 g) and a small amount,of concentrated hydrochloric acid were added and the atmosphere was replaced with hydrogen, followed by allowing the mixture to react at 3.5 atm at room temperature for 10.5 hours. Then 10% palladium-carbon was removed through Celite and the filtrate was concentrated. The residue was again dissolved in methanol (30 ml) and 10% palladium-carbon (10 g) and a small amount of hydrochloric acid were added. The atmosphere was replaced with hydrogen, and the mixture was allowed to react at 3.5 atm at room temperature for 21 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated, followed by recrystallizing the residue from methanol/ether to obtain 2.38g of 4-diphenylmethylpiperidine hydrochloride. Yield: 38%.

Provenance & Evidence