Benzoyl chloride → N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-benzoyloxyethylthio)acetamide

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Reaction Steps

0.24 ml of benzoyl chloride was added, whilst ice-cooling, to a mixture of 0.40 g of N-[4-(4-piperidinomethyl -2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide (prepared as described in Example 1) and 1.02 ml of pyridine, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was concentrated by evaporation under reduced pressure. The concentrate was diluted with water and made alkaline by the addition of an aqueous ammonia solution, after which it was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:40 by volume mixture of methanol and ethyl acetate as the eluent, to give 0.31 g of the title compound in a 61% yield.

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