Triethylamine → N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Participants

Reaction Steps

To a solution of 1,3-diacetoxymethyl-5-[2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzene (synthesized in Example 33) (222 mg) dissolved in dichloromethane (4 mL) was added triethylamine (0.11 mL). 2-Furoyl chloride (0.06 mL) was added to the solution under ice cooling. The temperature was allowed to rise to room temperature, and the solution was stirred for 1 hour. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)] to give N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (276 mg). This product was subjected to the subsequent step without further purification.

Provenance & Evidence