N,N-Diethylethylenediamine → HCID 25139755, compound

Participants

Reaction Steps

A solution of chloride 206 (250 mg, 1.12 mmol) and N1,N1-diethylethane-1,2-diamine (0.63 mL, 4.48 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 (5-10%) of MeOH/DCM to give the 1-oxide 209 (255 mg, 75%) as a yellow solid: mp 150-151° C.; 1H NMR δ 8.09 (t, J=1.6 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 5.90 (br s, 1H, NH), 4.72 (t, J=8.3 Hz, 2H, H-7), 3.48-3.54 (m, 2H, CH2N), 3.30 (dt, J=8.3, 1.4 Hz, 2H, H-8), 2.69-2.72 (m, 2H, CH2N), 2.59 (q, J=7.1 Hz, 4H, 2×CH2), 1.05 (t, J=7.1 Hz, 6H, 2×CH3); 13C NMR δ 166.5, 159.3, 151.8, 129.3, 126.3, 116.6, 102.1, 72.9, 51.3, 46.7 (2), 38.7, 28.6, 11.7 (2). Anal. calcd for C15H21N5O2.¼CH3OH: C, 58.8; H, 7.1; N, 22.5. Found: C, 58.8; H, 6.7; N, 22.8%.

Provenance & Evidence