2-Morpholinoethylamine → N-[2-(4-Morpholinyl)ethyl]-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-amine 1-Oxide

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Reaction Steps

2-(4-Morpholinyl)ethylamine (3.93 mL, 30.0 mmol) was added to a stirred solution of chloride 21 (2.21 g, 10.0 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 3 h. The solvent was evaporated and the residue stirred with water (150 mL) at room temperature for 30 min. The solid was filtered, washed with water (3×10 mL) and dried to give 1-oxide 44 (3.08 g, 98%) as an orange solid: mp (water) 178-179° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.39 (s, 1H, H-5), 5.79 (br s, 1H, NH), 3.72 (br t, J=4.6 Hz, 4H, CH2O), 3.59 (q, J=5.6 Hz, 2H, CH2N), 2.97-3.05 (m, 4H, H-6, H-8), 2.63 (t, J=5.9 Hz, 2H, CH2N), 2.51 (br t, J=4.6 Hz, 4H, CH2N), 2.10-2.19 (m, 2H, H-7); 13C NMR δ 158.6, 154.6, 148.7, 143.3, 129.8, 120.5, 114.6, 66.9 (2), 56.8, 53.3 (2), 37.5, 33.1, 32.3, 25.7. Anal. calcd for C16H21N5O2: C, 60.9; H, 6.7; N, 22.2. Found: C, 61.0; H, 6.8; N, 22.3%.

Provenance & Evidence