Toluene → 1-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine

HRID 502701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502701
I[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C(OCC)(=O)C.O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[CH2:18][CH2:17]1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 531671-MethylpiperazineHCID 108529273-Iodo-5-nitrobenzotrifluorideHCID 23676156Sodium t-butoxide

Produkt 1

HCID 594280371-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Into a 50 mL round bottom flask was placed the 1-iodo-3-nitro-5-(trifluoromethyl)benzene (1 g, 3.15 mmol), N-methylpiperazine (0.379 g, 3.78 mmol), bis(dibenzylideneacetone)palladium (0.029 g, 0.0315 mmol), sodium tert-butoxide (0.424 g, 4.416 mmol), 2-dicyclohexyl-2′-(N,N-dimethylamino)biphenyl (0.037 g, 0.094 mmol), and toluene (25 mL). Reaction was heated to 80° C. with stirring for 20 hours. Reaction was cooled to room temperature and water (1 mL) and ethyl acetate (10 mL) were added. The organic layer is separated, concentrated under reduced pressure and purified via silica column eluting with 0 to 20% methanol in dichloromethane. The title compound was obtained as an orange oil.

Aufarbeitung

  1. customInto a 50 mL round bottom flask was placed
  2. customReaction
  3. customReaction
  4. temperaturewas cooled to room temperature
  5. customThe organic layer is separated
  6. concentrationconcentrated under reduced pressure
  7. custompurified via silica column
  8. washeluting with 0 to 20% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b2eb7fa5ef4f49e2acb762ffdd6afeee
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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