Tryptamine → 2-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide

Participants

Reaction Conditions

Reaction Steps

1-Hydroxybenzotriazole (182 mg, 1.35 mmol), tryptamine (108 mg, 0.676 mmol) and N-methylmorpholine (0.148 ml, 1.35 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (200 mg, 0.676 mmol) in dry dimethylformamide (10 ml) under argon. The clear solution was cooled to 0° C. and dicyclohexylcarbodiimide (278 mg, 1.35 mmol) was added. The reaction mixture was stirred at RT for 3 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). Still further urea thereby precipitated out and was separated off. The filtrate obtained was extracted with ether. 5 M sodium hydroxide solution (2 ml, 10 mmol) was added to the aqueous phase and the mixture was diluted with water (150 ml). The product thereby precipitated out as a colourless solid in a yield of 31% (84 mg).

Provenance & Evidence