Trifluoroacetic acid → 1-(2,6-Difluorophenyl)-5,5-dimethylpiperazin-2-one

HRID 1694928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694928
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][C:19](=[O:21])[N:18]([C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=2[F:29])[CH2:17][C:16]1([CH3:31])[CH3:30])=O)(C)(C)C>C(Cl)Cl>[F:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:29])[C:22]=1[N:18]1[CH2:17][C:16]([CH3:30])([CH3:31])[NH:15][CH2:20][C:19]1=[O:21]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 666456784-(2,6-Difluorophenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 666456401-(2,6-Difluorophenyl)-5,5-dimethylpiperazin-2-oneAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4.2 ml of trifluoroacetic acid (54.7 mmol) was added to a solution of 1.80 g of 4-(2,6-difluorophenyl)-2,2-dimethyl-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (60c) (5.47 mmol) in methylene chloride (8.4 ml) at room temperature, and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate aqueous solution was added, followed by extraction with methylene chloride. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=10/1) to obtain 1.25 g of the title compound (yield: quant.).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA saturated sodium bicarbonate aqueous solution was added
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-0b6746c79ff34b0fb3a0743e6530d50a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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