N,N-Dimethylethylenediamine → HCID 25140917, compound

Participants

Reaction Steps

A solution of chloride 206 (100 mg, 0.45 mmol) and N1,N1-dimethylethane-1,2-diamine (0.2 mL, 1.8 mmol) in DME (10 mL) was stirred at reflux temperature for 1 h, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (5-8%) of MeOH/DCM to give the 1-oxide 207 (108 mg, 88%) as a yellow solid, mp 163-165° C.; 1H NMR δ 8.09 (t, J=1.4 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 5.83 (br s, 1H, NH), 4.72 (t, J=8.3 Hz, 2H, H-7), 3.52-3.56 (m, 2H, CH2N), 3.31 (dt, J=8.3, 1.4 Hz, 2H, H-8), 2.57 (t, J=8.3 Hz, 2H, CH2N), 2.29 [s, 6H, N(CH3)2]; 13C NMR δ 166.5, 159.3, 151.8, 129.3, 126.4, 116.6, 102.0, 72.9, 57.6, 45.0 (2), 38.6, 28.6. HRMS (FAB+) calcd for C13H18N5O2 (MH+) m/z 276.1461, found 276.1461.

Provenance & Evidence