반응 #466738

반응 방정식

4-(6-Bromonaphth-2-ylsulphonyl)piperazine hydrochloride

4-(4-Pyridyl)benzoic acid

triethylamine

Carbonyldiimidazole

→

1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine

수율 14.0%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   온도then cooled to 5° C
2. 2
   온도to warm slowly to room temperature over one hour
3. 3
   workup.STIRRINGthe reaction mixture stirred for 2 days at room temperature
4. 4
   세척washed twice with saturated aqueous sodium hydrogen carbonate solution (2×50 mL)
5. 5
   건조The organic layer was dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo

실험 절차

4-(4-Pyridyl)benzoic acid (238 mg,1.2 mmol) was suspended in DMF (5 mL) with triethylamine (0.17 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 15 minutes then cooled to 5° C. Carbonyldiimidazole (194 mg, 1.2 mmol) was added and the reaction mixture allowed to warm slowly to room temperature over one hour. 4-(6-Bromonaphth-2-ylsulphonyl)piperazine hydrochloride (470 mg, 1.2 mmol) was added as a solid in one portion and the reaction mixture stirred for 2 days at room temperature. The reaction mixture was diluted with ethyl acetate (50 mL) and washed twice with saturated aqueous sodium hydrogen carbonate solution (2×50 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was subjected to chromatography (SiO2; 2%, 4%, 6%. 8%, 10% methanol/ethyl acetate) to yield 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine as a white solid (90 mg), 1H NMR (DMSO-d6) δ=3.07 ppm (s,4H), δ=3.59 ppm (s,4H), δ=7.27 & 7.46 ppm (dd,4H), δ=7.18 & 8.64 ppm (dd,4H), δ=7.34 ppm (m,2H), δ=8.17 ppm (dd,2H), δ=8.39 ppm (d,1H), δ=8.47 ppm (s,1H); MS (M+H)+ 536.

출처