반응 #84598

반응 방정식

NaBH(OAc)3

4-(2-aminoethyl)benzenesulfonamide

AcOH

isoquinoline-1-carbaldehyde

DCE

→

4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide

수율 77.0%

용매

water

반응 조건

후처리

1. 1
   추출The reaction mixture was extracted with DCM
2. 2
   기타The organic layer was dried
3. 3
   농축concentrated under reduced pressure
4. 4
   기타The residue was purified by flash chromatography over silica gel

실험 절차

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.0 g, 5.0 mmol), AcOH (1.0 mL) and isoquinoline-1-carbaldehyde (2.09 g, 13.3 mmol) in DCE (50 mL) was stirred at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford 4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide (1.86 g, 77%). 1H NMR (400 MHz, DMSO-d6) 8.24 (d, J=8.8 Hz, 2H), 7.96 (d, J=8.4 Hz, 2H), 7.91 (d, J=8.0 Hz, 2H), 7.72 (t, J=7.8 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.55 (t, J=7.6 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 7.30 (d, J=6.0 Hz, 2H), 7.29 (s, 2H), 4.01 (s, 4H), 2.94 (t, J=7.0 Hz, 2H), 2.78 (t, J=7.0 Hz, 2H); MS (ESI), 483.3 (M+H)+.

출처