Skatole → HCID 44514435, compound

Participants

Reaction Steps

3-methyl-1H-indole (393 mg, 3 mmol) and the 4-dimethylamino-1-(3-methoxyphenyl)-4-phenylcyclohexanol (651 mg, 2 mmol) mixture were dissolved in absolute dichloromethane (50 ml) with exclusion of oxygen, mixed with trifluoromethane sulphonic acid (581 μl, 3 mmol) and stirred for 16 h at room temperature. For work up the batch was mixed with 5N NaOH (50 ml) and stirred for 1 h at room temperature. The aqueous phase was separated and extracted with dichloromethane (3×25 ml). The combined organic phases were dried over Na2SO4 and then concentrated to low volume. A raw product was isolated that was purified by chromatography [silica gel 60 (50 g); ethyl acetate (500 ml)]. The product was obtained as a white solid with a yield of 90 mg (10%) and a melting point of 278-281° C. This concerned one of two possible diastereoisomers.

Provenance & Evidence