Ethanol → 3-(benzyloxy)propan-1-amine

Participants

Reaction Steps

To 20.5 g(0.1 mol) of the compound prepared in Preparation 5-1) in 40 ml of dimethylformamide was added 4.4 g(0.11 mol) of sodium hydride(60%). 18.9 g(0.11 mol) of benzyl bromide was added and the resulting mixture was reacted for 12 hours. After removal of solvent the reaction, solvent was removed and the residue was dissolved in ethylacetate and the organic layer was washed with saturated sodium bicarbonate solution. After removal of solvent, 200 ml of ethanol and 12.5 g(0.25 mol) of hydrazine hydrate was added thereto, and the resulting mixture was refluxed for 3 hours. After the reaction, solvent was removed under reduced pressure. The residue was dissolved in 200 ml of dichloromethane and the organic layer was washed with saturated sodium bicarbonate solution. 200 ml of 1N aqueous hydrochloric acid solution was added and the organic layer was removed. To the aqueous layer was added 200 ml of dichloromethane, and the resulting solution was basified with 6N sodium hydroxide solution. The organic layer was separated and the solvent was removed under reduced pressure to give 8.3 g(Yield 50%) of the title compound.

Provenance & Evidence