N-(3-Aminopropyl)morpholine → HCID 25140918, compound

Participants

Reaction Steps

A solution of chloride 206 (250 mg, 1.1 mmol) and 3-(4-morpholinyl)propylamine (0.65 mL, 4.5 mmol) in DME (25 mL) was stirred at reflux temperature for 2 h, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (2-5%) of MeOH/DCM, to give 1-oxide 211 (340 mg, 92%) as a yellow solid: mp 152-154° C.; 1H NMR δ 8.10 (t, J=1.6 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 6.09 (br s, 1H, NH), 4.42 (t, J=8.3 Hz, 2H, H-7), 3.75 (t, J=4.7 Hz, 4H, 2×CH2O), 3.55-3.60 (m, 2H, CH2), 3.30 (dt, J=8.3, 1.6 Hz, 2H, H-7), 2.46-2.52 (m, 6H, 2×CH2N, CH2), 1.82 (p, J=6.5 Hz, 2H, CH2); 13C NMR δ 166.5, 159.4, 151.8, 129.2, 126.4, 116.6, 102.1, 72.9, 67.0 (2), 57.3, 53.8 (2), 40.8, 28.6, 25.3. Anal. calcd for C16H21N5O3: C, 58.0; H, 6.4; N, 21.1. Found: C, 57.8; H, 6.2; N, 21.1%.

Provenance & Evidence