Dimethyl Sulfoxide → 4-[7-(3-Piperidin-1-yl-propoxy)-3,4-dihydro-1H-isoquinoline-2-sulfonyl]-benzamide

Participants

Reaction Steps

A 1.4 mL DMSO mixture of K2CO3 is stirred under N2, 2-(4-cyanobenzenesulfonyl)-7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline (75 mg, 0.17 mmol) is added, 0.2 mL H2O added, followed by 30% H2O2 (1.4 mL, 12 mmol) and reaction is stirred at room temperature for 4 hours. The reaction mixture is diluted with MeOH, filtered, and the solids washed twice with MeOH. The filtrate is concentrated and the residue is purified by chromatography (SCX-MeOH wash, elute 2M NH3/MeOH; then SiO2; 0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give the product as an off-white solid (26 mg, 26% yld). MS (ES+)458.2(M+H)+.

Provenance & Evidence