N,N-Dimethylethylenediamine → HCID 25140757, compound

HRID 1669138Notes

Reaction equation

HRID 1669138 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:23])[C:11]2[CH:17]=[C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][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-:23])[C:11]2[CH:17]=[C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:15]3=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 25139750HCID 25139750, compound

Product 1

HCID 25140757HCID 25140757, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N,N-Dimethyl-1,2-ethanediamine (0.23 mL, 2.1 mmol) was added to a stirred solution of chloride 187 (178 mg, 0.7 mmol) in DME (30 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 (0-10%) of MeOH/DCM, to give 1-oxide 188 (204 mg, 95%) as a yellow solid: mp (MeOH) 149-152° C.; 1H NMR δ 7.96 (s, 1H, H-11), 7.31 (s, 1H, H-5), 5.84 (br s, 1H, NH), 3.52-3.57 (m, 2H, CH2N), 2.85-2.90 (m, 4H, H-6, H-10), 2.58 (br t, J=6.0 Hz, 2H, CH2N), 2.28 [s, 6H, N(CH3)2], 1.79-1.85 (m, 2H, H-8), 1.65-1.74 (m, 4H, H-7, H-9); 13C NMR δ 159.0, 153.4, 148.0, 142.1, 129.0, 125.0, 118.8, 57.6, 45.1 (2), 38.7, 36.8, 36.2, 32.0, 28.7, 28.4. Anal. calcd for C16H23N5O.½H2O: C, 61.9; H, 7.8; N, 22.6. Found: C, 62.0; H, 7.8; N, 22.4%.

Workup

  1. temperatureat reflux temperature for 2 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-11d5ec11fb8a4d358be4a3723ebfb9bb
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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