Trimethylsilyl triflate → N,N-dimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

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Reaction Steps

Trifluoromethane sulphonic acid trimethylsilyl ester (755 mg, 617 μL, 3.4 mmol) was added to a suspension of 4-dimethylamino-1-[3-(1H-indol-3-yl)propyl]-4-phenylcyclohexanol (320 mg, 0.85 mmol) in absolute dichloromethane (20 mL), wherein a clear brown solution formed that was stirred for 14 d at room temperature. The reaction solution was then diluted with dichloromethane (10 mL), washed with 1 N sodium carbonate solution (2×10 mL), water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (270 mg) was mixed with methanol (30 mL) and stirred overnight at room temperature, wherein a light-coloured solid formed, which was filtered off and washed with a little methanol (2 mL).

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