Hydrochloric Acid → 4-(1-Adamantylmethyl)piperidine hydrochloride

Participants

Reaction Steps

A mixture of 4-(1-adamantylmethyl)pyridine (500 mg, 2.20 mmol) and PtO2 (15 mg) in MeOH (20 mL) containing concd HCl (1 mL) was allowed to shake under H2 (25-30 psi) for 24 h. NMR analysis showed only about 45% reaction. An additional portion of catalyst was added and the reaction was allowed to proceed as above for an additional 24 h. The analysis now showed about 70% reaction. The reaction was allowed to proceed at 50 psi for a final 24 h (72 h total). A crystalline solid was observed in the reaction mixture. The addition of CH2Cl2 and warming dissolved this material. The analysis now showed ˜95% reaction. The catalyst was removed by filtration (Celite) and the solvent was removed to give a yellow solid. The solid was dissolved in boiling MeOH (12 mL) and the solution was hot filtered. The filtrate was concd to 8 mL and was cooled in an ice bath to give a suspension. The solid was collected, was washed with ice cold MeOH (3×1 mL) and was dried in vacuo (100° C., 0.005 Torr) to give the title compound as a pale yellow crystalline solid (365 mg, 62%): mp >300° C.; 1H NMR (DMSO-d6) 0.95 (d, J =4.5, 2H), 1.22-1.78 (m, 17H), 1.90 (s, 3H), 2.81 (dd, J=22 and 11, 2H), 3.13 (d, J=12, 2H), 8.68 (bs, 1H), 8.89 (bs, 1H).

Provenance & Evidence