Reacción #7230

Ecuación de reacción

N-(2-pyridinylmethyl)-N-(2-nitrobenzenesulfonyl)-N′-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

thiophenol

K2CO3

→

title compound

Rendimiento 82.0%

N-(2-pyridinylmethyl)-N′-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Rendimiento 82.0%

Disolventes

CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroPurification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH)

Procedimiento

Using general procedure C: N-(2-pyridinylmethyl)-N-(2-nitrobenzenesulfonyl)-N′-(4-methoxy-5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.269 g, 0.50 mmol) was treated with thiophenol (0.35 mL, 3.41 mmol) and K2CO3 (0.757 g, 5.48 mmol) in CH3CN (10 mL). Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.158 g (82%) of the title compound as a yellow oil. 1H NMR (CDCl3) □ 1.61–1.80 (m, 2H), 1.98–2.17 (m, 2H), 2.56–2.70 (m, 2H), 3.79–3.83 (m, 6H), 3.88–3.98 (m, 4H), 6.60 (d, 1H, J=5.7 Hz). 7.15 (dd, 1H, J=5.1, 6.9 Hz), 7.23–7.41 (m, 5H) 7.63 (ddd, 1H, J=7.8, 7.8, 1.8 Hz), 8.30 (d, 1H, J=5.7 Hz); 8.55 (d, 1H, J=3.9 Hz);

Fuente