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

HRID 1108577노트

반응식

HRID 1108577 반응식
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][C:4]1=[O:9])[CH3:2].C(N(CC)C(C)C)(C)C.[F:19][C:20]1[CH:21]=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=[CH:24][C:25]=1F.FC(F)(F)C(O)=O.C(N(CC)C(C)C)(C)C>C(#N)C>[F:19][C:20]1[CH:21]=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=[CH:24][C:25]=1[N:6]1[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[C:4](=[O:9])[CH2:5]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 98773661-Ethylpiperazin-2-oneHCID 12593398N,N-diisopropylethylamine trifluoroacetate

생성물 1

HCID 187839123-Fluoro-4-(4-ethyl-3-oxopiperazin-1-yl)nitrobenzene

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-Ethyl-2-oxopiperazine (3TFA salt, 10.5 g) was dissolved in acetonitrile (200 ml), and N,N-diisopropylethylamine (19.5 ml) followed by 3,4-difluoronitrobenzene (2.25 ml) were added. The mixture was 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 a solid containing some N,N-diisopropylethylamine trifluoroacetate. The solid was purified by dissolving in ethyl acetate and washing well with water. Evaporation of the organic layer gave 3-fluoro-4-(4-ethyl-3-oxopiperazin-1-yl)nitrobenzene as a solid (3.44 g).

후처리

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 18 hours
  4. customSolvent was evaporated
  5. customthe residue chromatographed on silica using as eluant
  6. temperaturea gradient increasing in polarity from 0 to 4% methanol in dichloromethane
  7. customevaporated
  8. customto give a solid
  9. customThe solid was purified
  10. dissolutionby dissolving in ethyl acetate
  11. washwashing well with water
  12. customEvaporation of the organic layer

출처 및 근거

ORD 기록
ord-e6d6bb280fdc4ebf98f0251e68132f1e
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069145

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