Potassium Carbonate → 1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol

HRID 515279

Reaktionsgleichung

Reaktionsgleichung von HRID 515279
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1>C(#N)C>[F:33][C:32]([F:34])([F:35])[C:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:12]2[CH2:11][CH2:10][C:9](=[CH:8][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:16][CH:15]=3)[CH2:14][CH2:13]2)=[CH:26][CH:27]=1)([OH:40])[C:36]([F:37])([F:39])[F:38]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 67194164HCID 67194164, Verbindung

Produkt 1

HCID 866709361,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-olAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 4-(4-nitrobenzylidene)piperidine (23.83 mmol, 5.2 g) and potassium carbonate (31.0 mmol, 4.28 g) in acetonitrile was added a solution of 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (23.83 mmol, 8.03 g) in acetonitrile. The reaction was stirred for 5 hours then was concentrated under reduced pressure. Dichloromethane was added and the reaction was filtered. The filtrate was chromatographed on silica (eluting with a gradient of dichloromethane to dichloromethane/ethyl acetate) to give the title compound (7.3 g).

Aufarbeitung

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe reaction was filtered
  4. customThe filtrate was chromatographed on silica (
  5. washeluting with a gradient of dichloromethane to dichloromethane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e8d41c0a48d644ea9543f9f9bf56fdfd
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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