تفاعل #84598

معادلة التفاعل

NaBH(OAc)3

4-(2-aminoethyl)benzenesulfonamide

AcOH

isoquinoline-1-carbaldehyde

DCE

→

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

المردود 77.0%

المذيبات

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)+.

المصدر