Trimethylsilyl triflate → 6-fluoro-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 (822 mg, 671 μL, 3.70 mmol) was added to a suspension of 4-dimethylamino-1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-phenyl-cyclohexanol (365 mg, 0.92 mmol) in absolute dichloromethane (50 mL), and stirred for 10 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), the organic phase dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (249 mg) was mixed with methanol (50 mL) and stirred over the weekend 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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