Triethylamine → HCID 53831000, compound

Participants

Reaction Steps

Oxalyl chloride (3.50 ml) was added to a suspension of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-3-phenylbut-2-enoic acid dihydrochloride (4.17 g, 9.81 mmol) in dichloromethane (50 ml) and a few drops of dry N,N-dimethyl formamide added. After stirring at room temperature for 3 h, the solid formed was filtered off and a solution of triethylamine (3.07 g, 30.4 mmol) and hexamethyleneimine (1.07 g, 10.8 mmol) in dichloromethane (25 ml) was added dropwise to an ice-cooled suspension of the filtered solid in dichloromethane (50 ml). The reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The crude product was chromatographed on silica gel, eluting with ethyl acetate: pentane (1:1 to 2:1) to afford the title compound as two isomers. The Z-isomer was obtained as an oil and this was dissolved in diethyl ether and acidified with ethereal hydrogen chloride to afford a colourless hygroscopic powder which was recrystallised from dichloromethane-diisopropylether to give the dihydrochloride as a colourless powder (0.36 g), m.p. 149.4° to 152.9° C.

Provenance & Evidence