Methyl iodide → [4-Methoxy-4-(3-methoxy-prop-1-ynyl)-1-phenyl-cyclohexyl]-dimethylamine

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Methyl propargyl ether (1.47 g, 21.0 mmol) dissolved in abs. THF (15 mL) was added in drops to a 2.5 M solution of butyl lithium in hexane (8.4 mL, 21.0 mmol) at −30° C. in argon. A solution of 4-dimethylamino-4-phenylcyclohexanone (4.34 g, 20.0 mmol) in abs. THF (20 mL) and lithium bromide (0.87 g, 10 mmol) dissolved in abs. THF (2.5 mL) was then added at −30° C. The reaction mixture was heated to −5° C., mixed drop by drop with a solution of methyl iodide (4.25 g, 30 mmol) in abs. DMSO (25 mL) and stirred for 2 h at 50° C. For work up of the reaction mixture water (30 mL) was added with ice bath cooling and extracted with cyclohexane (4×50 mL). The organic phase was washed with 20% ammonium chloride solution, dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with CHCl3/MeOH (20:1).

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