HCID 12760485, compound → HCID 12760487, compound

Participants

Reaction Steps

N,N-Dihexadecyl-4-(aminomethyl)phenoxy acetamide (2.8 g, 0.0042 mole) was dissolved in benzene (30 ml) and treated with sodium bis-(2-methoxyethoxy)-aluminum hydride (5.94 g of a 70% solution in benzene). The mixture was refluxed for 16 hours, cooled and quenched with 10% sodium hydroxide solution (10.2 ml). The organic phase was separated, washed with saturated sodium chloride solution (3×50 ml), dried over sodium sulfate, filtered and concentrated under vacuum to an oil (2.27 g). The product was purified by silica gel chromatography (eluted with a chloroform/ethanol gradient mixture), converted to the hydrochloride salt, and recrystallized from ethanol/acetonitrile (1:1) to give the desired ethyl amine (0.725 g, 25% yield), mp 231°-238° C.

Provenance & Evidence