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

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Reaction Steps

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);

Provenance & Evidence