Sodium Iodide → (4-Cyano-4-(3-cyano-5-thienyl)-5-methylhexyl]-4-[2-(4-cyanophenoxy)ethyl]piperazine

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Reaction Steps

In acetonitrile (5 ml) was dissolved 4-cyano-4-(3-cyano-5-thienyl)-5-methylhexanol (0.13 g). To the mixture were added triethylamine (0.21 ml) and mesyl chloride (0.048 ml), followed by stirring at room temperature for one hour. Water was added thereto, and the mixture was extracted with ethyl acetate and further washed with brine. After drying over anhydrous magnesium sulfate, the mixture was evaporated, to give a pale yellow oil. The resulting oil was dissolved in DMF (2 ml), followed by adding a DMF solution (4 ml) of 1-[2-(4-cyanophenoxy)ethyl]piperazine (0.14 g), triethylamine (0.21 ml) and sodium iodide (0.15 g). After stirring at 60° C. overnight, ethyl acetate was added thereto, and the mixture was washed with water and further brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by NH silica gel column chromatography (hexane/ethyl acetate system), to give the title compound as a pale yellow oil (0.09 g, 33%).

Provenance & Evidence