1,4-Cyclohexanedione → HCID 67275119, Verbindung

HRID 2172186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172186
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[C:19]1(=O)[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1>[Pd].C(O)C>[F:18][C:2]([F:17])([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)=[CH:15][CH:16]=1

Komponenten

5

Edukt 2

HCID 125111,4-CyclohexanedioneHCID 23081575HCID 23081575, Verbindung

Produkt 1

HCID 67275119HCID 67275119, VerbindungAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

10% palladium on carbon (64 mg) was added to an ethanol solution (13 ml) of 4-(4-trifluoromethoxybenzyl)piperidine (1.28 g) and 1,4-cyclohexanedione (1.19 g), and the mixture was stirred at 70 to 80° C. for 8.5 hours. After being cooled to room temperature, the catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. After being dissolved in ethyl acetate, the residue was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After being concentrated under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4) to afford the title compound as a black oil (305 mg).

Aufarbeitung

  1. temperatureAfter being cooled to room temperature
  2. customthe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionAfter being dissolved in ethyl acetate
  5. washthe residue was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter being concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→6:4)

Quellen und Nachweise

ORD-Eintrag
ord-cf96a904f7bc4cee9e8328e307e9cf53
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051333B2

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