4-Methylmorpholine → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide

Participants

Reaction Conditions

Reaction Steps

1-Hydroxybenzotriazole (819 mg, 6.0 mmol), 5-(1H-indol-3-yl)pentylamine (606 mg, 3.0 mmol) and N-methylmorpholine (0.666 ml, 6.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (887 mg, 3.0 mmol) in dry dimethylformamide (10 ml) under argon. The solution was cooled to 0° C. and dicyclohexylcarbodiimide (1.25 g, 6.0 mmol) was added. The reaction mixture was stirred at RT for 4 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 aqueous phase was diluted with water (300 ml), 5 M sodium hydroxide solution (7 ml, 35 mmol) was added and the mixture was stored at 5° C. for 3 d. The crude product thereby precipitated out as a beige-coloured solid in a yield of 69% (915 mg). After chromatography on silica gel (50 mg) with EA/methanol (1:1) and methanol, the product was isolated as a colourless solid (333 mg) with an m.p. of 68-72° C. in a yield of 25%.

Provenance & Evidence