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1,3-Dinitrobenzene → Tert-butyl 4-(3-fluoro-4-nitrophenyl)piperazine-1-carboxylate

HRID 1496962
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HRID 1496962 반응식
[N+:1](C1C=C([N+]([O-])=O)C=CC=1)([O-:3])=[O:2].C(N1CCNCC1)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[C:49]([F:51])[CH:48]=[CH:47][C:46]=2[N+]([O-])=O)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]>CN(C)C=O>[C:32]([O:36][C:37]([N:39]1[CH2:40][CH2:41][N:42]([C:45]2[CH:46]=[CH:47][C:48]([N+:1]([O-:3])=[O:2])=[C:49]([F:51])[CH:50]=2)[CH2:43][CH2:44]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 74521,3-DinitrobenzeneHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22272537tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

생성물 1

HCID 66738172Tert-butyl 4-(3-fluoro-4-nitrophenyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
50 °C

실험 절차

2,4-dinitrobenzene (1.2 g), N-Boc-piperazine (1.4 g) and potassium carbonate (1.2 g) were dissolved in dimethylformamide (5 mL) and stirred at 50° C. overnight. Then, the mixture was distilled under reduced pressure to remove dimethylformamide, added with water, and extracted with ethyl acetate. The thus obtained organic layer was washed with brine, and water was removed with sodium sulfate, and the solvent was removed by distillation under reduced pressure. The mixture was purified by column chromatography (silica gel) to obtain target compounds (Rf=0.3, hexane:ethyl acetate=2:1) and (tert-butyl-4-(5-fluoro-2-nitrophenyl)piperazin-1-carboxylate (Rf=0.6, hexane:ethyl acetate=2:1).

후처리

  1. distillationThen, the mixture was distilled under reduced pressure
  2. customto remove dimethylformamide
  3. additionadded with water
  4. extractionextracted with ethyl acetate
  5. washThe thus obtained organic layer was washed with brine, and water
  6. customwas removed with sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe mixture was purified by column chromatography (silica gel)
  9. customto obtain target compounds (Rf=0.3, hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-33434855225a4960ab79bee64b09fab3
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199944B2

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