2-Chlorobenzyl chloride → Ticlopidine Hydrochloride

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Reaction Steps

26.1 g of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine, 80 ml of ethanol and 19 g of sodium bicarbonate are charged into a 250-ml three-necked round bottom flask fitted with a thermometer, a condenser and a mechanical stirrer. 30.2 g of o-chlorobenzyl chloride are then added and the mixture is heated to about 75°-80° C. during 1 hour. The reaction mixture is evaporated down and the residue is taken up with 200 ml of isopropyl ether. The 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine obtained is then added to 100 ml of ethanol. After adding 20 ml of concentrated hydrochloric acid to the ethanolic solution, heating to reflux and cooling the mixture, 46.6 g of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride, which crystallises, are obtained.

Provenance & Evidence