Hydrochloric Acid → HCID 70623876, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.42 g. (0.01 mole) of 3-(2-cyanothioxanthen-9-ylidene)quinolizidine in 50 ml. of benzene is added to a stirred solution of 0.013 mole of methyl magnesium bromide in 5 ml. of ether and 50 ml. of benzene. The stirred mixture is heated at reflux temperature for two hours, then it is cooled to 10° C. and added slowly to 250 ml. of vigorously stirred ice-water. Excess 3 N hydrochloric acid is added to the stirred mixture. The aqueous layer is separated and then it is made alkaline with 2.5 N sodium hydroxide. The mixture is extracted with ethyl acetate. After being dried over magnesium sulfate, the extracts are concentrated. The residue is chromatographed on an alumina column using ether as the eluate. Evaporation of the appropriate fractional eluant gives 3-(2-acetylthioxanthen-9-ylidene)quinolizidine which is converted to a fumarate salt by treatment with a molar equivalent of fumaric acid in methanol.

Provenance & Evidence