Potassium Iodide → 4-(2,3,4-Trimethoxybenzylthio)-1-cinnamylpiperidine fumarate

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Reaction Steps

A mixture of 10 g of 4-(2,3,4-trimethoxybenzylthio)piperidine and 6.62 g of cinnamyl bromide in 300 ml of CH3CN is heated under reflux for 15 hours in the presence of 4.64 g of potassium carbonate and 0.5 g of potassium iodide. The salt is then filtered off and the filtrate is evaporated under reduced pressure. The residue is taken up in CH2Cl2 --H2O and, after decantation, the ichloromethane phase is dried over Na2SO4 and evaporated under reduced pressure. The resulting residue (15 g) is purified by chromatography on 600 g of silica with a toluene-methanol (95-5) system, yielding 10 g of crude base, which is converted into the fumarate in an ethanol medium. 7 g of 4-(2,3,4-trimethoxybenzylthio)-1-cinnamylpiperidine fumarate are obtained in the form of white crystals which melt at 129° C.

Provenance & Evidence