tert-Butyl piperazine-1-carboxylate → 4-(5-Nitro-2-trifluoromethoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1710600

Reaktionsgleichung

Reaktionsgleichung von HRID 1710600
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=1[O:57][C:58]([F:61])([F:60])[F:59].[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:64])[CH3:63].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:62]([O:66][C:67]([N:69]1[CH2:74][CH2:73][N:72]([C:48]2[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=2[O:57][C:58]([F:61])([F:60])[F:59])[CH2:71][CH2:70]1)=[O:68])([CH3:65])([CH3:63])[CH3:64]

Komponenten

7

Edukt 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 247216412-Bromo-4-nitro(trifluoromethoxy)benzene

Produkt 1

HCID 670947894-(5-Nitro-2-trifluoromethoxy-phenyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 0.048 g palladium(II)-acetate (0.214 mmol) and 0.133 g BINAP (0.214 mmol) in 7 mL toluene was heated to 60° C., stirred for 10 min. and the obtained suspension was added dropwise to a solution of 0.51 g 2-bromo-4-nitro-1-(trifluoromethoxy)benzene (1.783 mmol), 0.343 g tert.butyl-piperazine-1-carboxylate (1.842 mmol) and 0.232 g sodium tert-butoxide (2.414 mmol) in 8 mL of toluene. The thus obtained reaction mixture was treated at 130° C. for 1.5 h in a commercial microwave oven. The organic layer was washed with water, the aqueous phase was extracted with dichloromethane and the combined organic layers were extracted with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was further purified via silica gel chromatography using a ISCO Companion system (eluent cyclohexane-ethyl acetate 5-25%) to yield 0.413 g of product.

Aufarbeitung

  1. customThe thus obtained reaction mixture
  2. additionwas treated at 130° C. for 1.5 h in a commercial microwave oven
  3. washThe organic layer was washed with water
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. extractionthe combined organic layers were extracted with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe crude product was further purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-33e18adf3c554e2bb7578855c5491576
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790727B2

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