Aniline → HCID 178463271, compound

Participants

Reaction Steps

To a solution of Trans-N-(4-acetylcyclohexyl)-2-chloro-5-(trifluoromethyl)-benzamide (200 mg, 0.57 mmol) and aniline (54 mg, 0.57 mmol) in DCM (10 mL) is added DMF (0.1 mL) followed by trichlorosilane (78 mg, 0.57 mmol). After stirring at room temperature for 1 hour, further trichlorosilane (5×78 mg, 5×0.57 mmol) is added at 1 hour intervals for the next 5 hours. Further DMF (0.1 mL) was then added and the mixture is stirred at room temperature overnight. The colourless solid that is formed is recovered by filtration, washed successively with water and then EtOAc and dried. [MH+ 425.38]. The racemic mixture was separated by supercritical fluid chromatography on chiral stationary phase analogously to that reported for Example 1.37.

Provenance & Evidence