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Acetonitrile → 1-[[Bis(4-methoxyphenyl)phenyl]methyl]piperidine

HRID 80311
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80311
COC1[CH:24]=[CH:23][C:6]([C:7](Cl)([C:16]2[CH:21]=[CH:20]C=CC=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=CC=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[C:31](#N)[CH3:32]>CCCCCC>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[C:6]([C:32]3[CH:31]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)=[C:23]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:20]=[CH:21][CH:16]=2)=[CH:13][CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 8082PiperidineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Produkt 1

HCID 674283821-[[Bis(4-methoxyphenyl)phenyl]methyl]piperidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

4,4′-dimethoxytrityl chloride (0.83 g, 2.45 mmol) (Tokyo Chemical Industry Co., Ltd.) was dissolved in acetonitrile (15 mL) (Wako Pure Chemical Industries, Ltd.), and piperidine (1.24 g, 14.6 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was refluxed for 1 hour, and the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was washed with water and brine. After that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to alumina column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.)→chloroform (Wako Pure Chemical Industries, Ltd.):n-hexane (Wako Pure Chemical Industries, Ltd.)=1:4 as an eluent), to thereby obtain the title compound (0.81 g, 85% yield).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 hour
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionA saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture
  4. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c52c9f022bb8424eb2280ab9945dda9f
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846012B2

Notizen zur Reaktion

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