Potassium Iodide → HCID 13253839, compound

Participants

Reaction Steps

A mixture of 2.0 g of 3-(4-chlorophenyl)-1,3-dihydrospiro[benzo(c)thiophene-1,4'-piperidine], Example 15, 0.7 g of chloromethylcyclopropane, 1.4 g of potassium iodide and 1.4 g of sodium bicarbonate in 20 ml of dimethylformamide is heated with stirring at 80°-85° C. for 17 hours. The reaction mixture is permitted to cool to ambient temperature before being diluted with 75 ml of water and 30 ml of methylene chloride. The aqueous phase is extracted twice with methylene chloride and all the methylene chloride solutions are combined. The combined solutions are washed, sequentially, with water and saturated sodium chloride solution and then dried effecting a clear oil. The oil is chromatographed on an alumina column with an ether eluant to obtain the oil with enhanced purity. This oil is converted to its maleic acid salt which is recrystallized from an acetone-ether mixture to obtain the salt, mp 217.5°-218° C. of 3-(4-chlorophenyl)-1'-cyclopropylmethyl-1,3-dihydrospiro[benzo(c)thiophene-1,4'-piperidine] maleate.

Provenance & Evidence