Tryptamine → 3-[2-(3-Indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid ethyl ester

Participants

Reaction Steps

To a solution of 1.45 g of the butyric acid obtained in 30 ml of dichloromethane was added 0.86 g of 1,1'-carbonyldiimidazole. The mixture was stirred for 1 hour at room temperature. Then, 0.82 g of triptamine was added to the reaction mixture, and the mixture was stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed successively with water, diluted hydrochloric acid and water, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate/benzene=1/1 by volume) to obtain 1.41 g of 3-[2-(3-indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid ethyl ester as a light brown powder.

Provenance & Evidence