Chlorosulfonic acid → HCID 90449895, compound

Participants

Reaction Steps

1-(1′-Acetylspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (1.19 g, 3.81 mmol) was dissolved in methylene chloride (10 mL). Thereafter, chlorosulfonic acid (1.27 mL, 19 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred for 30 minutes. Thereafter, while stirring, the reaction solution was added dropwise to ice water, and was then extracted with chloroform. The obtained organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was dissolved in methylene chloride (20 mL). Thereafter, N,N-diisopropylethylamine (0.7 mL, 4 mmol) and 1-methylpiperazine (0.22 mL, 2 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 15 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with chloroform. The obtained organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was dissolved in methanol (3 mL), and a saturated solution of ammonium-methanol (3 mL) was then added to the above obtained solution, followed by stirring the mixture at room temperature for 30 minutes. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 1-(5-((4-methylpiperazin-1-yl)sulfonyl)spiro[indoline-3,3′-pyrrolidin]-1′-yl)ethanone (559 mg, 82%) in the form of a white solid.

Provenance & Evidence