Xanthene-9-carboxylic acid → N-[1-(cyclooctylmethyl)piperidin-4-yl]xanthene-9-carboxamide

Participants

Reaction Steps

4.71 g of 4-amino-1-t-butoxycarbonylpiperidine hydrochloride and 4.50 g of xanthene-9-carboxylic acid were suspended in 150 ml of anhydrous N,N-dimethylformamide, and 5.5 ml of triethylamine was added thereto. The mixture was cooled in ice and 5.73 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter referred to as EDCI.HCl) and 4.04 g of 1-hydroxybenzotriazole were successively added thereto. The temperature was raised to room temperature immediately, and the reaction solution was stirred for 12 hours. After the reaction solution was cooled to 0° C., 80 ml of water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with 10% citric acid solution, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 7.78 g of the title compound as a white solid was obtained.

Provenance & Evidence