Water → HCID 59529925, compound

Participants

Reaction Steps

To a solution of 500 mg of indole-2-carboxylic acid and 530 mg of ethyl piperidin-3-yl acetate in 8 mL of DMF were added 610 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 430 mg of 1-hydroxybenzotriazole, followed by stirring at room temperature for 2 hours. 0.5M aqueous hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with 0.5M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 519 mg of ethyl[1-(1H-indol-2-ylcarbonyl)piperidin-3-yl]acetate. To a solution of 392 mg of the resulting ethyl[1-(1H-indol-2-ylcarbonyl)piperidin-3-yl]acetate in 7 mL of THF was added 30 mg of lithium borohydride, followed by stirring at room temperature for 1 day. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:0-2:1], and then crystallized from diisopropyl ether to obtain 92 mg of 2-[1-(1H-indol-2-ylcarbonyl)piperidin-3-yl]ethanol as a white solid.

Provenance & Evidence