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

HRID 1496962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1496962
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-33434855225a4960ab79bee64b09fab3
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09199944B2

Notizen zur Reaktion

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