Acetic Anhydride → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide

Participants

Reaction Conditions

Reaction Steps

0.50 g of N-[4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide (prepared as described in Example 1) was added to a mixture of 0.47 ml of acetic anhydride and 0.39 g of pyridine, and the resulting mixture was heated at 60° C. for 2 hours. At the end of this time, the reaction mixture was poured into ice-water, after which a saturated aqueous solution of sodium hydrogencarbonate was added. The aqueous mixture was then extracted with chloroform. The extract was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and methylene chloride as the eluent, to give 0.51 g (yield 91%) of the title compound as an oil.

Provenance & Evidence