N,N-Dimethylethylenediamine → HCID 25140910, compound

HRID 1669146Notes

Reaction equation

HRID 1669146 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][CH2:20][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][CH2:20][C:15]3=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 25139751HCID 25139751, compound

Product 1

HCID 25140910HCID 25140910, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N,N-Dimethyl-1,2-ethanediamine (0.40 mL, 3.6 mmol) was added to a stirred solution of chloride 196 (270 mg, 1.2 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 4 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 (0-10%) of MeOH/DCM, to give 1-oxide 197 (216 mg, 65%) as a yellow solid: mp (MeOH/EtOAc) 153-157° C.; 1H NMR δ 7.50 (s, 1H, H-9), 7.40 (t, J=1.4 Hz, 1H, H-5), 5.73 (br s, 1H, NH), 4.67 (t, J=8.3 Hz, 2H, H-7), 3.48-3.53 (m, 2H, CH2N), 3.53 (dt, J=8.3, 1.4 Hz, 2H, H-6), 2.55 (dd, J=6.1, 5.9 Hz, 2H, CH2N), 2.28 [s, 6H, N(CH3)2]; 13C NMR δ 158.3, 158.2, 146.1, 140.6, 130.6, 121.8, 96.6, 71.9, 57.7, 45.1 (2), 38.8, 29.7. Anal. calcd for C13H17N5O2.¼CH3OH: C, 56.2; H, 6.4; N, 24.7. Found: C, 56.1; H, 6.2; N, 25.0%.

Workup

  1. temperatureat reflux temperature for 4 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-14d9bb0b30384823ad49fe330e301887
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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