N-(3-Aminopropyl)morpholine → HCID 25139621, compound

Participants

Reaction Steps

3-(4-Morpholinyl)propylamine (314 mg, 2.18 mmol) was added to a stirred solution of chloride 176 (171 mg, 0.73 mmol) in DME (8 mL) and the solution stirred at reflux temperature for 30 min. The solution was cooled and partitioned in between EtOAc and aqueous Na2CO3 solution. The organic fraction was washed with water, dried and the solvent evaporated to give 1-oxide 179 (250 mg, 100%) as an orange solid: mp (EtOAc) 115-116° C.; 1H NMR δ 7.97 (s, 1H, H-10), 7.29 (s, 1H, H-5), 6.14 (br s, 1H, NH), 3.75 (t, J=4.6 Hz, 4H, 2×CH2O), 3.60 (q, J=6.2 Hz, 2H, CH2N), 2.86-2.95 (m, 4H, H-6, H-9), 2.45-2.56 (m, 6H, 3×CH2N), 1.80-1.88 (m, 6H, H-7, H-8, CH2); 13C NMR δ 158.7, 147.5 147.0, 136.0, 129.1, 124.9, 119.0, 67.0 (2), 57.3, 53.8 (2), 40.8, 30.0, 29.3, 25.3, 22.7, 22.5. Anal. calcd for C18H25N5O2: C, 63.0; H, 7.3; N, 20.4. Found: C, 62.8; H, 7.4; N, 20.3%.

Provenance & Evidence