Sodium Carbonate → HCID 68708429, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-bromopropyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared in an analogous manner as described in general procedure V), 1-Boc-piperazine (624 mg, 3.35 mmol, 6 equiv.), sodium carbonate (granular, 355 mg, 3.35 mmol, 6 equiv.), and ethanol (5 mL) in a sealed reaction vessel was heated at 90° C. for 8 h. After cooling, solid sodium carbonate was removed by decantation, and the supernatant was concentrated and re-dissolved in ethyl acetate (15 mL). The resulting solution was washed with water, dried (anhydrous sodium sulfate), and concentrated. The crude oil was pre-adsorbed onto Florisil and purified via Isco flash column chromatography (4-g redisep silica gel column, 5-60% ethyl acetate/hexane) to give 252 mg (96%) of tert-butyl 4-[3-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)propyl]piperazine-1-carboxylate as a viscous, brown liquid. MS (ESI) m/z 473.1 ([M+H]+).

Provenance & Evidence