Cyclohexene → 4-(2-Methoxyphenyl)piperidine

Participants

Reaction Steps

A solution of 1-benzyloxycarbonyl-4-(2-methoxyphenyl)piperidine (0.67 g) in ethanol (10 mL) was treated with cyclohexene (4.2 mL) followed by 10% palladium on carbon (0.13 g). After heating to reflux for 2 hours, the reaction mixture was cooled to room temperature, diluted with ether and extracted with 1N hydrochloric acid. The aqueous layer was made basic with sodium bicarbonate and extracted with dichloromethane. The organic layers were dried over anhydrous sodium sulfate and evaporated to afford the piperidine (0.2 g); NMR (CDCl3): 1.60 (d of q, 2, J1 =12, J2 =4), 1.73-1.82 (broad, 2), 2.74-2.83 (d of t, 2, J1 =12, J2 =2), 3.02-3.2 (m, 3), 3.82 (s, 3), 6.85 (d, 1, J=8), 6.9 (m, 1), 7.15-7.26 (m, 2); MS: m/z=192(M+1). This material was used in the next step without further purification.

Provenance & Evidence