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Ethyl Acetate → 1-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine

HRID 856099
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 856099
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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.O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:26]3[CH:25]=[CH:24][C:23]([O:22][C:21]([F:20])([F:30])[F:31])=[CH:28][CH:27]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=1
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Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 230811571-[4-(Tetrahydropyran-2-yloxy)phenyl]piperazineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 230811991-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazineAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 634876Binap, (A+-)-KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-[4-(tetrahydropyran-2-yloxy)phenyl]piperazine (2.1 g, 8.05 mmol) prepared in Reference Example 184, 4-trifluoromethoxy-1-bromobenzene (1.9 g, 8.05 mmol), palladium acetate (72 mg, 0.32 mmol), BINAP (300 mg, 0.48 mmol) and sodium tert-butoxide (1.0 g, 10.5 mmol) in toluene (30 ml) was refluxed under a nitrogen atmosphere for 5 hours. Ethyl acetate and water were added to the reaction mixture, which was stirred for a while. The insoluble substances were removed by filtration through Celite, and the filtrate was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1) to afford 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine (3.1 g, yield 90%) as a white powder.

Aufarbeitung

  1. temperaturewas refluxed under a nitrogen atmosphere for 5 hours
  2. customThe insoluble substances were removed by filtration through Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-892e1928eb744cea86788614b5a5f33e
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07262212B2

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