Trifluoroacetic acid → 5,5-Dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-one

HRID 1694944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694944
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[CH3:29])[CH2:17][C:16]1([CH3:31])[CH3:30])=O)(C)(C)C>C(Cl)Cl>[CH3:30][C:16]1([CH3:31])[CH2:17][N:18]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[CH3:29])[C:19](=[O:21])[CH2:20][NH:15]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 666457692,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 666457455,5-Dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10 ml of trifluoroacetic acid (134 mmol) was added to a solution of 4.5 g of 2,2-dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazine-1-carboxylic acid t-butyl ester obtained in Example (70c) (13.4 mmol) in methylene chloride (20 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 2.71 g of the title compound (yield: 86%).

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-4dfe31eb0afa4ae9ae02824b57aa3051
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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