Triethylamine → N-[3-(5-fluoro-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine

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Reaction Steps

To a stirred suspension of 0.29 g of 3-(5-fluoro-3-pyridyl)acrylic acid in 15 ml of dry tetrahydrofuran, 0.24 g of triethylamine is added at room temperature. The resulting solution is cooled to between -10° C. and -5° C., and a solution of 0.25 g of ethyl chloroformate in 2 ml of tetrahydrofuran is added slowly. After the mixture is stirred at the same temperature for 2 hours, a solution of 0.75 g of 4-(4-diphenylmethyl-1-piperazinyl)butylamine in 2 ml of dry tetrahydrofuran is added. The mixture is stirred for 1 hour at between -10° C. and -5° C. and then at room temperature overnight. The insoluble materials are filtered off, and the filtrate is concentrated. The residue is chromatographed on silica gel with chloroform-methanol (40:1) to give 0.3 g of the title compound. m.p. 128°-129° C. (recrystallized from toluene-hexane)

Provenance & Evidence