1-(2-Azido-2-methylpropyl)-4-(trifluoromethyl)benzene → 2-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amine

HRID 1504293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504293
[N:1]([C:4]([CH3:17])([CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[N+]=[N-].[H][H]>C(OCC)(=O)C.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[CH3:17][C:4]([NH2:1])([CH3:16])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1

Komponenten

5

Edukt 2

HCID 866974731-(2-Azido-2-methylpropyl)-4-(trifluoromethyl)benzeneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1209942-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amineAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178420936HCID 178420936, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

25.4 g of 1-(2-azido-2-methylpropyl)-4-(trifluoromethyl)benzene was dissolved in 210 mL of ethyl acetate and mixed with 0.84 g of 20 wt % palladium hydroxide carbon. The atmosphere in the reaction vessel was replaced with hydrogen gas, and the reaction solution was stirred at room temperature for 18 hours. After completion of the reaction, the palladium hydroxide carbon was filtered off, and the filtrate was mixed with 3 M hydrochloric acid and separated. The aqueous layer was basified with 5 M sodium hydroxide and extracted with methylene chloride. The organic layer was concentrated under reduced pressure to give 4.27 g of the desired product as a brown liquid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe palladium hydroxide carbon was filtered off
  3. additionthe filtrate was mixed with 3 M hydrochloric acid
  4. customseparated
  5. extractionextracted with methylene chloride
  6. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8fabf58c9874edb937b5488ad91c802
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212348B2

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