N,N-Dimethylethylenediamine → HCID 25138705, compound
Reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:21])[C:11]2[CH:17]=[C:16]3[O:18][CH2:19][O:20][C:15]3=[CH:14][C:12]=2[N:13]=1>COCCOC>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:8]1[N:9]=[N+:10]([O-:21])[C:11]2[CH:17]=[C:16]3[O:18][CH2:19][O:20][C:15]3=[CH:14][C:12]=2[N:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N,N-Dimethyl-1,2-ethanediamine (0.52 mL, 4.8 mmol) was added to a stirred solution of chloride 222 (359 mg, 1.6 mmol) in DME (40 mL) and the solution stirred at reflux temperature for 2 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-15%) of MeOH/DCM, to give 1-oxide 223 (390 mg, 88%) as a yellow solid: mp (MeOH/DCM) 192-194° C.; 1H NMR δ 7.45 (s, 1H, H-9), 7.35 (br s, 1H, NH), 6.96 (s, 1H, H-5), 6.23 (s, 2H, H-7), 3.35-3.39 (m, 2H, CH2N), 2.42 (t, J=6.7 Hz, 2H, CH2N), 2.18 [s, 6H, N(CH3)2]; 13C NMR δ 158.9, 155.2, 148.7, 146.9, 125.3, 103.2, 101.6, 95.9, 57.8, 45.2 (2), 38.6. Anal. calcd for C12H15N5O3: C, 52.0; H, 5.5; N, 25.3. Found: C, 52.1; H, 5.5; N, 25.3%.
Workup
- temperatureat reflux temperature for 2 h
- customThe solvent was evaporated
- customthe residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL)
- customThe organic fraction was dried
- customthe solvent evaporated
- customThe residue was purified by chromatography
- washeluting with a gradient (0-15%) of MeOH/DCM
Sources & evidence
- ORD record
- ord-f711b4df80b8425e8595039b82de9008
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989451B2
Reaction notes
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