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

Participants

Reaction Steps

To a solution of 2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclooctyl]ethanol (synthesized in Example 73) (0.53 g) in tetrahydrofuran (7 mL) were added triethylamine (0.79 mL) and 2-furoyl chloride (0.35 mL) successively. The solution was stirred at room temperature for 1 hour. To the reaction solution was added methanol (7 mL) and a 3N aqueous potassium hydroxide solution (4.7 mL), and it was stirred at room temperature for 15 hours. 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, methanol-chloroform (5:95)] to give the title compound (0.55 g).

Provenance & Evidence