Methanol → 3-(1H-Imidazol-5-yl)piperidine

Participants

Reaction Conditions

Reaction Steps

A 100-mL round-bottomed flask was charged with a solution of benzyl 3-(1H-imidazol-5-yl)piperidine-1-carboxylate (3 g, 10.53 mmol, 1.00 equiv) in 1,4-dioxane (30 mL) and conc. HCl (18 mL). The resulting mixture was heated to 80° C. in an oil bath for 16 hours. The reaction progress was monitored by TLC (DCM: MeOH=10:1). Upon completion, the resulting mixture was concentrated on a rotary evaporator. The resulting solution was diluted with water (60 mL) and treated with aqueous NaHCO3. The resulting mixture was then extracted with dichloromethane (4×40 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator affording 3-(1H-imidazol-5-yl)piperidine as brown oil (0.5 g, 31%).

Provenance & Evidence