Triethylamine → N-[1-[2-[4-(2-Hydroxyethyl)tetrahydropyran-4-yl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

Participants

Reaction Steps

To a solution of 2-[4-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]tetrahydropy-ran-4-yl]ethanol (synthesized in Example 80) (239 mg) in tetrahydrofuran (3 mL) was added triethylamine (0.29 mL) and 2-furoyl chloride (0.17 mL) sucessively. The reaction solution was stirred at room temperature for 30 minutes. To the reaction solution were added methanol (4 mL) and a 3N aqueous potassium hydroxide solution (2 mL). The reaction solution was stirred at room temperature for additional 15 minutes. Water was added to the reaction solution and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, chloroform-methanol (30:1)] to give the title compound (210 mg).

Provenance & Evidence