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Potassium Carbonate → tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylate

HRID 586770
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 586770
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 22336105tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4.65 g (3.10 mmol) of 2-fluoro-5-nitrotoluene, 6.71 g (3.60 mmol) of tert-butyl 1-piperazinecarboxylate and 10.4 g (7.50 mmol) of potassium carbonate are solubilized under an argon atmosphere, in dry DMF (50 ml), then the reaction medium is taken to 80° C. for 18 hours. The reaction medium is then cooled down using an ice bath then poured into ice-cold water. The product is extracted using 3 times 50 ml of ethyl acetate. The organic solution is dried over magnesium sulphate, followed by filtration and concentration under vacuum. Purification is then carried out by crystallization from diisopropyl ether and the solid obtained is filtered and rinsed with isopentane in order to obtain, after drying, 5.9 g of a yellow solid product (yield 62%). Melting point: 121.8-123.4° C.

Aufarbeitung

  1. temperatureThe reaction medium is then cooled down
  2. additionthen poured into ice-cold water
  3. extractionThe product is extracted
  4. dry with materialThe organic solution is dried over magnesium sulphate
  5. filtrationfollowed by filtration and concentration under vacuum
  6. customPurification
  7. customis then carried out by crystallization from diisopropyl ether
  8. customthe solid obtained
  9. filtrationis filtered
  10. washrinsed with isopentane in order
  11. customto obtain
  12. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-6b658cff99964004beade35b7bebd8f3
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06936715B2

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