1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol → HCID 86670937, Verbindung

HRID 515280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515280
[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][C:19](=[CH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H][H]>[Pd].C(OCC)(=O)C>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:3]([OH:8])([C:4]([F:7])([F:5])[F:6])[C:2]([F:1])([F:32])[F:33])=[CH:10][CH:11]=3)[CH2:21][CH2:20]2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 2

HCID 866709361,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-olHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86670937HCID 86670937, VerbindungAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred mixture of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(4-nitrobenzylidene)piperidin-1-yl)methyl)phenyl)propan-2-ol (15.39 mmol, 7.3 g) and palladium on carbon (5%) (0.308 mmol, 0.328 g) in ethyl acetate was hydrogenated at 3 bar until the desired amount of hydrogen was consumed. The mixture was filtered through celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica (eluting with a gradient of dichloromethane to ethyl acetate) to give the title compound (4.3 g). MS (ESI) m/z 447.2 [M+H]+

Aufarbeitung

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. washthrough celite washing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica (
  6. washeluting with a gradient of dichloromethane to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-81b62cf1718e4f91bae9aa5a527b2a49
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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