4-Piperidinemethanol → (1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethenyl}piperidin-4-yl)methanol

HRID 1620553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620553
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13](=O)[CH3:14].[NH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]1.C(=O)([O-])O.[Na+]>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)=[CH2:14]

Komponenten

6

Edukt 3

HCID 4207714-PiperidinemethanolHCID 516892Sodium BicarbonateHCID 27360932',4'-Bis(trifluoromethyl)acetophenone

Produkt 1

HCID 86678734(1-{1-[2,4-Bis(trifluoromethyl)phenyl]ethenyl}piperidin-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1-[2,4-bis(trifluoromethyl)phenyl]ethanone (10.0 g) and piperidin-4-ylmethanol (5.40 g) in THF (368 mL) was added titanium (IV) isopropoxide (34.6 mL). The reaction mixture was stirred at 70° C. overnight, and poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution and the insoluble material was filtered through celite. The organic layer of the filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound so (12.6 g).

Aufarbeitung

  1. additionpoured into ice-
  2. filtrationthe insoluble material was filtered through celite
  3. customThe organic layer of the filtrate was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-44146fc3094d4054b3a04efe28f86119
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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