N,N-Dimethylethylenediamine → HCID 25139886, compound

HRID 1669170Notes

Reaction equation

HRID 1669170 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].Cl[C:8]1[N:9]=[N+:10]([O-:22])[C:11]2[C:21]3[CH2:20][CH2:19][CH2:18][O:17][C:16]=3[CH:15]=[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-:22])[C:11]2[C:21]3[CH2:20][CH2:19][CH2:18][O:17][C:16]=3[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 25138866HCID 25138866, compound

Product 1

HCID 25139886HCID 25139886, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N,N-Dimethyl-1,2-ethanediamine (65 μL, 0.6 mmol) was added to a stirred solution of chloride 235 (47 mg, 0.2 mmol) in DME (20 mL) and the solution stirred at reflux temperature for 2 h. The solvent was evaporated and the residue was partitioned between DCM (50 mL) and dilute aqueous NH3 solution (20 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 236 (55 mg, 95%) as a pale yellow solid: mp (MeOH/EtOAc) 119-120° C.; 1H NMR δ 7.35 (d, J=9.2 Hz, 1H, H-6), 7.23 (d, J=9.2 Hz, 1H, H-5), 5.66 (br s, 1H, NH), 4.19 (br dd, J=5.1, 5.0 Hz, 2H, H-8), 3.47-3.53 (m, 4H, H-10, CH2N), 2.54 (br t, J=6.0 Hz, 2H, CH2N), 2.27 [s, 6H, N(CH3)2], 1.97-2.04 (m, 2H, H-9); 13C NMR δ 158.0, 152.2, 146.7, 130.3, 128.4, 125.2, 114.0, 65.9, 57.7, 45.1 (2), 38.7, 24.9, 22.2. Anal. calcd for C14H19N5O2.¼H2O: C, 57.2; H, 6.7; N, 23.8. Found: C, 57.5; H, 6.6; N, 23.8%.

Workup

  1. temperatureat reflux temperature for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between DCM (50 mL) and dilute aqueous NH3 solution (20 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-f3063785fa3d43a689d111c659ea65f8
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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