Hydrochloric Acid → HCID 69457928, compound

Participants

Reaction Steps

To a solution of 2-{3-[(2R)-2-aminopropyl]-1H-indol-7-yl}-N,N-diethylacetamide (1.0 g, 3.48 mmol) in dimethylsulfoxide (5 mL) is added N-trimethylsilylacetamide (0.50 g, 3.83 mmol), and the mixture is stirred at room temperature for 1 hour. To the reaction solution is added (R)-(+)-3-chlorostyrene oxide (0.89 mL, 6.96 mmol), and the mixture is stirred at 110° C. for 2 hours. After cooling, a 2 N hydrochloric acid (5 mL) is added to the mixture, and the mixture is stirred at room temperature for 0.5 hour. To the mixture are added a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and the mixture is extracted with chloroform. The organic layer is dried over anhydrous sodium sulfate and concentrated. The residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform) to give the title compound (0.90 g, yield: 59%).

Provenance & Evidence