N,N-Dimethylethylenediamine → HCID 10244493, compound

Participants

Reaction Steps

N,N-Dimethyl-1,2-ethanediamine (1.33 mL, 12.1 mmol) was added to a stirred solution of chloride 7 (0.85 g, 4.04 mmol) in DME (50 mL) and the solution stirred at reflux temperature for 16 h. The solvent was evaporated and the residue was partitioned between DCM (100 mL) and dilute aqueous NH3 (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give amine 8 (0.72 g, 68%) which was dissolved in HCl-saturated MeOH, the solvent evaporated and the residue crystallized as a tan solid, mp (MeOH/EtOAc) 236-239° C.; 1H NMR [(CD3)2SO] δ 10.68 (br s, 1 H, NH+Cl−), 8.07 (d, J=9.3 Hz, 1 H, H-8), 8.03 (br s, 1 H, NH), 6.95-6.99 (m, 2 H, H-5, H-7), 3.92 (s, 3 H, OCH3), 3.70-3.76 (m, 2 H, CH2N), 3.30-3.35 (m, 2 H, CH2N), 2.81 [d, J=4.9 Hz, 6 H, N(CH3)2]; 13C NMR [(CD3)2SO] δ 164.9, 159.0, 150.4, 125.4, 121.6, 117.3, 104.3, 55.2, 55.0, 42.3 (2), 35.8. Anal. Calcd for C12H18ClN5O2: C, 48.1; H, 6.1; N, 23.4; Cl, 11.8. Found: C, 48.3; H, 6.1; N, 23.6; Cl, 11.9%.

Provenance & Evidence