Hydrochloric Acid → HCID 70036578, compound

Participants

Reaction Conditions

Reaction Steps

To a suspended solution of 4-(3-indolyl)piperidine (200 mg, 1.0 mmol) in dichloromethane (15 mL) was added pyridine (5 mL), and the resulting mixture was cooled to 0° C. Subsequently, 3-chloropropionyl chloride (0.25 mL, 2.6 mmol) was then added dropwise to the mixture, and the resulting mixture was stirred at 0° C. for 2 hours. After the reaction mixture was poured into hydrochloric acid and then extracted with ethyl acetate, the ethyl acetate layer was washed with 1 N hydrochloric acid and a saturated aqueous sodium chloride and was dried over anhydrous sodium sulfate. After sodium sulfate was filtered off, the filtrate was concentrated to afford a crude product (100 mg). After identifying the structure of the crude product by 1H NMR and IR, piperidine (350 mg, 4.0 mmol) was added to a solution of the crude product in acetonitrile (10 mL), and the mixture was stirred at 80° C. for 3 hours. After concentrating the reaction mixture, water (10 mL) was added thereto, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:2) to afford a free form (97 mg, yield: 29%) of the title compound as a colorless amorphous solid. After adding hydrochloric acid/methanol to a solution of the free form (67 mg) in methanol, the mixture was concentrated and was then reprecipitated from ethanol/ether to afford the title compound (50 mg) as a pale yellow amorphous solid.

Provenance & Evidence