Water → 4-(4-Methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 1031547

Reaktionsgleichung

Reaktionsgleichung von HRID 1031547
[H-].[Na+].[OH:3][C:4]1([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1.[F:18][C:19]1[C:24](F)=[C:23]([F:26])[C:22]([F:27])=[C:21]([F:28])[C:20]=1[F:29].O>CN(C)C=O>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([C:4]2([O:3][C:24]3[C:23]([F:26])=[C:22]([F:27])[C:21]([F:28])=[C:20]([F:29])[C:19]=3[F:18])[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]2)=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 9805HexafluorobenzeneHCID 24758Sodium hydrideHCID 148370371-Methyl-4-(4-methylphenyl)piperidin-4-OL

Produkt 1

HCID 148370634-(4-Methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a suspension of sodium hydride (2.2 g, 60% in oil) in 20 ml of dimethylformamide, was added a solution of 11.0 g of 4-hydroxy-4-(4-methylphenyl)-1-methylpiperidine in 50 ml of dimethylformamide. After heating to 85° C. for thirty minutes, the mixture was cooled with an ice-bath, and treated over a period of ten minutes with a solution of 7 ml of hexafluorobenzene in 20 ml of dimethylformamide. After stirring at ambient temperature for twenty hours, the mixture was poured into 200 ml water, stirred for five minutes, then extracted with ethyl acetate (2×). The organic layer was washed with water (2×), followed by a saturated solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the solvent afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichloromethane). The desired fractions were combined, and evaporated to yield 13 g of (4-(4-methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil.

Aufarbeitung

  1. temperaturethe mixture was cooled with an ice-bath
  2. stirringstirred for five minutes
  3. extractionextracted with ethyl acetate (2×)
  4. washThe organic layer was washed with water (2×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customevaporation of the solvent
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichloromethane)
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e892695c03d40eab71f96993ded0761
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954511

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