N,N-Diethylethylenediamine → HCID 25139755, compound

HRID 1669154Notes

Reaction equation

HRID 1669154 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:11]=[C:10]3[CH2:12][CH2:13][O:14][C:9]3=[CH:8][C:6]=2[N:7]=1.[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][NH2:21])[CH3:17]>COCCOC>[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][NH:21][C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:11]=[C:10]3[CH2:12][CH2:13][O:14][C:9]3=[CH:8][C:6]=2[N:7]=1)[CH3:17]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 25139754HCID 25139754, compound

Product 1

HCID 25139755HCID 25139755, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 206 (250 mg, 1.12 mmol) and N1,N1-diethylethane-1,2-diamine (0.63 mL, 4.48 mmol) in DME (25 mL) was stirred at reflux temperature for 2 h, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (5-10%) of MeOH/DCM to give the 1-oxide 209 (255 mg, 75%) as a yellow solid: mp 150-151° C.; 1H NMR δ 8.09 (t, J=1.6 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 5.90 (br s, 1H, NH), 4.72 (t, J=8.3 Hz, 2H, H-7), 3.48-3.54 (m, 2H, CH2N), 3.30 (dt, J=8.3, 1.4 Hz, 2H, H-8), 2.69-2.72 (m, 2H, CH2N), 2.59 (q, J=7.1 Hz, 4H, 2×CH2), 1.05 (t, J=7.1 Hz, 6H, 2×CH3); 13C NMR δ 166.5, 159.3, 151.8, 129.3, 126.3, 116.6, 102.1, 72.9, 51.3, 46.7 (2), 38.7, 28.6, 11.7 (2). Anal. calcd for C15H21N5O2.¼CH3OH: C, 58.8; H, 7.1; N, 22.5. Found: C, 58.8; H, 6.7; N, 22.8%.

Workup

  1. temperatureat reflux temperature for 2 h
  2. customthe solvent evaporated
  3. customthe residue purified by chromatography
  4. washeluting with a gradient (5-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-b2f01e6cfb5049718410e0c60aaefaf6
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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