Benzaldehyde → 4-Aminomethyl-1-N-Cbz-piperidine

Participants

Reaction Conditions

Reaction Steps

22.2 g(0.2 mol) of 4-aminomethyl piperidine was dissolved in 250 ml of toluene and 21.2 g(0.2 mol) of benzaldehyde was added thereto. The reaction mixture was heated to reflux for 3 hours with Dean-stack and then cooled down to 0° C. 34.2 g(0.2 mol) of benzyl chloroformate was added dropwise while stirring. The reactants were stirred for 3 hours and 220 ml of 1N KHSO4 was added at room temperature. The reaction solution was extracted with 200 ml of diethylether 3 times and the aqueous layer was basified with sodium hydroxide. After the aqueous solution was treated with saturated sodium chloride solution, it was extracted with 100 ml of dichloromethane 3 times. and the organic layer was dried over magnesium sulfate. Removal of dichloromethane under reduced pressure provided 38 g of the title compound(Yield 91%, MW 248).

Provenance & Evidence