4-Methylmorpholine → HCID 11597063, compound

Participants

Reaction Steps

1-Hydroxybenzotriazole (546 mg, 4.0 mmol), C-(1H-indol-3-yl)methylamine (292 mg, 2.0 mmol) and N-methylmorpholine (0.444 ml, 4.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (596 mg, 2.0 mmol) in dry dimethylformamide under argon. Dicyclohexylcarbodiimide (834 mg, 4.0 mmol) was added at 0° C. and the mixture was stirred at RT for 7 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). A mixture of urea and product thereby precipitated out (482 mg) and was separated off. The filtrate obtained was diluted with water (300 ml), 5 M sodium hydroxide solution (4 ml, 20 mmol) was added and the mixture was stored at 5° C. for 16 h. A crude product thereby precipitated out as a beige-coloured substance (234 mg), which was separated off by filtration. After purification of the two product fractions by chromatography on silica gel with EA/methanol (4:1) and methanol, the product was isolated as a beige-coloured solid in a yield of 30% (230 mg).

Provenance & Evidence