Hydrochloric Acid → 2-Benzylpiperidine hydrochloride

Participants

Reaction Steps

A solution of 2-benzylpyridine (2.0 g, 12 mmol) in MeOH (50 mL) containing conc. HCl (1 mL) was hydrogenated in a Parr apparatus over Pt (PtO2, 30 mg) at 25° C. The reaction was allowed to proceed at 22 psi for 5 h, 45 psi for 4 h, then overnight at 22 to 12 psi. The catalyst was removed by filtration and the solvent was removed in vacuo to give a syrup. Absolute EtOH (50 mL) was added and then evaporated in vacuo. This was repeated to give a near colorless solid. The solid was triturated with ether (2×20 mL) and dried in vacuo to give a colorless powder (2.36 g, 94% yield); mp 128-131° C., lit. 125-130° C. (vide supra); 1H NMR (D2O) 1.45-2.05 (m, 6H), 2.80-3.05 (m, 3H), 3.27-3.45 (m, 2H) 7.26-7.46 (m, 5H).

Provenance & Evidence