Hydrochloric Acid → HCID 67587995, compound

Participants

Reaction Steps

4-Formylcinnamic acid (1.76 g) and 1-(3-aminopropyl)-2-methylimidazole (2.78 g) were stirred in methanol (100 ml) for 5 hours at ambient temperature. Sodium borohydride (1.14 g) was added and the mixture stirred for 2 days at ambient temperature. The reaction mixture was evaporated to dryness. The residue was dissolved in water (60 ml) and washed with dichloromethane. The aqueous solution was neutralised with 5M hydrochloric acid and then washed with dichloromethane. The aqueous layer was evaporated to dryness to give crude 4-[3-(2-methylimidazol-1-yl)propylaminomethyl]cinnamic acid which was boiled under reflux in absolute ethanol (50 ml) and concentrated sulphuric acid (1.5 ml) with stirring for 20 hours. The mixture was hot filtered and the residue dissolved in water, basified with 2M sodium hydroxide and extracted into ethyl acetate to yield an oil which was dissolved in ether and treated with ethereal hydrogen chloride. The solid was collected by filtration and recrystallised from propan-2-ol to give ethyl 4-[3-(2-methylimidazol-1-yl)propylaminomethyl]cinnamate dihydrochloride, m.p. 109°-110.5° C.

Provenance & Evidence