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Binap, (A+-)- → 1-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazine

HRID 856097
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 856097
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Br[C:19]1[CH:31]=[CH:30][C:22]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:21][CH:20]=1.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[O:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[O:23][C:22]1[CH:30]=[CH:31][C:19]([N:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:16])[F:17])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)=[CH:20][CH:21]=1
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Komponenten

9

Edukt 4

HCID 634876Binap, (A+-)-HCID 46464362-(4-Bromophenoxy)tetrahydro-2H-pyranHCID 230811701-(4-(Trifluoromethoxy)phenyl)piperazineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 230811991-[4-(Tetrahydropyran-2-yloxy)phenyl]-4-(4-trifluoromethoxyphenyl)piperazineAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-trifluoromethoxyphenyl)-piperazine (4.4 g, 17.8 mmol), 2-(4-bromophenoxy)-tetrahydropyran (4.6 g, 17.8 mmol), palladium acetate (159 mg, 0.71 mmol), BINAP (666 mg, 1.07 mmol) and sodium tert-butoxide (2.2 g, 23.1 mmol) in toluene (40 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 then 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 (2.7 g, yield 35%) 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 then 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-5c2fe5f738a940adab0ec2714f488092
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07262212B2

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