Benzhydrylamine → 1-(Diphenylmethyl)azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of benzhydrylamine (200 ml, 1.6 mol) and epichlorohydrin (186 ml, 1 mol equivalent) in methanol (600 ml) was stirred at room temperature for five days and then heated at 40° C. for two days. The solvent was then removed under reduced pressure, the residue dissolved in isopropyl alcohol (500 ml) and the solution heated under reflux for six hours. The solution was cooled to room temperature and the precipitate filtered off. This solid was partitioned between dichloromethane (400 ml) and saturated aqueous sodium bicarbonate solution (500 ml). The aqueous phase was extracted with dichloromethane (2×400 ml), the combined organic extracts dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure to give the title product (86 g) as a crystalline solid. 1H-NMR (CDCl3): δ=1.8-2.3(s,br,1H), 2.85-2.9(m,2H), 3.5-3.55(m,2H), 4.35(s,1H), 4.4-4.5(m, 1H), 7.15-7.4(m,10H)ppm.

Provenance & Evidence