Potassium Iodide → 1-{2-[2-(3,4-Dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethyl}-4-phenylpiperidine-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

200 mg (0.36 mmole) of 2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol methanesulfonate [prepared as described in step (f) above], 105 mg (0.44 mmole) of 4-phenylpiperidine-4-carboxamide hydrochloride, 100 mg (1.19 mmole) of sodium hydrogencarbonate and 100 mg (0.60 mmole) of potassium iodide were suspended in 2 ml of dimethylformamide, and the mixture was then stirred under a stream of nitrogen at 80° C. for 6 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was then washed with an aqueous solution of sodium thiosulfate, with water and with a saturated aqueous solution of sodium chloride, in that order. The organic extract was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by thin-layer chromatography, using a 9:1 by volume mixture of methylene chloride and methanol as the developing solvent and then crystallized from hexane, to give 205 mg (yield 86%) of the title compound.

Provenance & Evidence