Diisopropylethylamine → HCID 22716473, compound

HRID 1108592Notes

Reaction equation

HRID 1108592 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, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Fluoroethyl)-2-oxopiperazine trifluoroacetate (6.1 g) was dissolved in acetonitrile (100 ml). N,N-Diisopropylethylamine (13 ml) was added to the mixture, followed by 3,4-difluoronitrobenzene (3.39 g), and the mixture heated to reflux for 18 hours. Solvent was evaporated, and the residue chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 4% methanol in dichloromethane. Relevant fractions were combined and evaporated to give 3-fluoro-4-(4-{2-fluoroethyl}-3-oxopiperazin-1-yl)nitrobenzene product as a solid (4.4 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 18 hours
  3. customSolvent was evaporated
  4. customthe residue chromatographed on silica
  5. temperaturea gradient increasing in polarity from 0 to 4% methanol in dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-c746c89f0b9c494896dd3c2d7cc8d7bc
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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