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Triethylamine → 1-[2,4-Bis(trifluoromethyl)phenyl]piperidine-4-carbaldehyde

HRID 1620589
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1620589
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CS(C)=O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][CH:16]([CH:19]=[O:20])[CH2:17][CH2:18]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86678761{1-[2,4-Bis(trifluoromethyl)phenyl]piperidin-4-yl}methanol

Produkt 1

HCID 866787621-[2,4-Bis(trifluoromethyl)phenyl]piperidine-4-carbaldehydeAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

To a solution of {1-[2,4-bis(trifluoromethyl)phenyl]piperidin-4-yl}methanol (2.41 g) and triethylamine (3.08 mL) in dimethyl sulfoxide (30 mL) was added sulfur trioxide pyridine complex (3.52 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.60 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fe0a1436ee6d488e971a297b926fb58b
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772277B2

Notizen zur Reaktion

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