Thionyl Chloride → N1-(S-(4-methoxybenzyl) thiosalicyloyl)-N4-methylpiperazine

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The compound N1-(S-(4-methoxybenzyl) thiosalicyloyl)-N4-methylpiperazine (compound 2) was prepared in a manner similar to that described above for S-(4-methoxybenzyl)-N-(2-(N′,N′-dimethylamino)ethyl) thiosalicylamide. After preparing the S-benzylthiosalicyloyl chloride from 0.02M(5.487 g) of S-(4-methoxybenzyl)thiosalicylic acid and 20 mL of SOCl2, the mixture was suspended in warm benzene (30 mL) and was slowly added to a 20 mL cold solution of 4.007 g (0.04M) 1-methylpiperazine in benzene. The mixture was stirred overnight at room temperature. The next day 40 mL of water were added, the aqueous layer was separated, and extracted twice with 15 mL CH2Cl2. The extracts were combined with the benzene layer, washed with 10% NaOH solution and dried over anhydrous MgSO4. Removal of the solvents under reduced pressure left an oily product which was dissolved in petroleum ether (10 ml). A precipitate separated out upon cooling in an ice bath. The separated solid was collected by suction filtration and washed with petroleum ether to give 3.372 g (47%) of the product in the form of white crystals and having a melting point of 77-78° C. and the following specifications:

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