Diisopropylethylamine → HCID 22716473, compound

HRID 1166013Notes

Reaction equation

HRID 1166013 reaction equation
FC(F)(F)C(O)=O.[F:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].C(N(CC)C(C)C)(C)C.[F:27][C:28]1[CH:29]=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[CH:32][C:33]=1F>C(#N)C>[F:27][C:28]1[CH:29]=[C:30]([N+:35]([O-:37])=[O:36])[CH:31]=[CH:32][C:33]=1[N:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][F:8])[C:12](=[O:17])[CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 22716476HCID 22716476, compound

Product 1

HCID 22716473HCID 22716473, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Fluoroethyl)-2-oxopiperazine trifluoroacetate (6.1 g) is dissolved in acetonitrile (100 ml). N,N-Diisopropylethylamine (13 ml) is added to the mixture, followed by 3,4-difluoronitrobenzene (3.39 g) and the mixture heated to reflux for 18 hours. The solvent is removed and the residue chromatographed (silica; eluting with a gradient increasing in polarity from 0 to 4% methanol in dichloromethane) to give 3-fluoro-4-(4-{2-fluoroethyl}-3-oxopiperazin-1-yl)nitrobenzene.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 18 hours
  3. customThe solvent is removed
  4. customthe residue chromatographed (silica
  5. washeluting with a gradient
  6. temperatureincreasing in polarity from 0 to 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5e0360dfac71424c9cd91d092aa031af
Source dataset
uspto-grants-2003_09
Patent number
US06613349B2

Reaction notes

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