Phenylacetaldehyde → HCID 20839307, compound

Participants

Reaction Steps

0.017 Mol of this phthalimido derivative was dissolved in ethanol and hydrazine hydrochloride (0.088 mol) was added. The mixture was heated at 100° C. for three hrs., then the reaction mixture was cooled, the phthalhydrazide formed during the reaction was removed by filtration and the filtrate was concentrated. The amino derivative obtained was purified by transforming it in ether into the hydrochloride to yield 70% of 2-[bis(4-fluorophenyl)methoxy]ethanamine hydrochloride. Equimolar amounts of 2-[bis(4-fluorophenyl)methoxy]-ethanamine hydrochloride, benzeneethanal and NaBH3CN were dissolved in dry tetrahydrofuran (50 ml for 0.01 mol) and a few ml of methanol were also added. The mixture was left at room temperature with stirring overnight. The solid material was filtered off, the filtrate was evaporated and the residue was dissolved in dichloromethane. This solution was dried with sodium sulfate, filtered and concentrated. The compound was purified by flash column chromatography by using a mixture of petroleum ether/ethyl acetate in a ratio 7:3 increasing to 6:4. The eluent was previously saturated with ammonia gas. The free base obtained was transformed into the (Z)-2-butenedioate by adding maleic acid in ether, which was crystallized from a mixture of ether and methanol (10:1) to give N-[2-(bis(4-fluorophenyl)-methoxy)ethyl]benzeneethanamine (Z)-2-butenedioate (1:1) salt. m.p. 145°-147° C.

Provenance & Evidence