Diisopropylethylamine → 3-Fluoro-4-(4-methyl-3-oxopiperazin-1-yl)nitrobenzene

HRID 1108568Notes

Reaction equation

HRID 1108568 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].[F:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1F>C(#N)C>[F:18][C:19]1[CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[CH:23][C:24]=1[N:14]1[CH2:15][CH2:16][N:11]([CH3:10])[C:12](=[O:17])[CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 43990421-Methylpiperazin-2-one

Product 1

HCID 187839263-Fluoro-4-(4-methyl-3-oxopiperazin-1-yl)nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (11.5 ml) and 1-methyl-2-oxopiperazine (4.12 g) were added to a solution of 3,4-difluoronitrobenzene (1.82 ml) in acetonitrile (100 ml), and the mixture heated to reflux for 16 hours. Solvent was evaporated, and the residue chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 100% ethyl acetate in iso-hexane. Relevant fractions were combined and evaporated to give 3-fluoro-4-(4-methyl-3-oxopiperazin-1-yl)nitrobenzene (3.37 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. customSolvent was evaporated
  4. customthe residue chromatographed on silica
  5. temperaturea gradient increasing in polarity from 0 to 100% ethyl acetate in iso-hexane
  6. customevaporated

Sources & evidence

ORD record
ord-f78ad015c006464ea31e376b16217840
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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