Sodium Hydroxide → 2-(5-Fluoro-2-{[4'-(trifluoromethyl)-1,1'-biphenyl-4-yl]methoxy}phenyl)ethylamine

HRID 1921898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921898
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[C:6]([CH2:8][C:9]#[N:10])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[C:6]([CH2:8][CH2:9][NH2:10])[CH:7]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 579719252-(5-Fluoro-2-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methoxy)phenyl)acetonitrile

Produkt 1

HCID 579719282-(5-Fluoro-2-{[4'-(trifluoromethyl)-1,1'-biphenyl-4-yl]methoxy}phenyl)ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

140.97 g (0.366 mol) of (5-fluoro-2-{[4′-(trifluoromethyl)-1,1′-biphenyl-4-yl]methoxy}phenyl)-acetonitrile are dissolved in 701 ml of anhydrous THF under argon and, after cooling to 0° C., 361.6 ml (0.362 mol) of a 1 M solution of lithium aluminum hydride in THF are added. Then 73.2 g (0.55 mol) of aluminum trichloride in 701 ml of THF are slowly added dropwise to the reaction solution. The reaction mixture is stirred at room temperature for 3.5 h. After reaction is complete, the solution is cooled to 0° C. and aqueous sodium hydroxide solution is slowly added. The aqueous phase is extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness in vacuo. The crude product is purified by chromatography on 10 kg of silica gel (mobile phase: dichloromethane/methanol 6:4). 90.28 g (61% of theory) of the title compound are obtained.

Aufarbeitung

  1. customAfter reaction
  2. temperaturethe solution is cooled to 0° C.
  3. extractionThe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude product is purified by chromatography on 10 kg of silica gel (mobile phase: dichloromethane/methanol 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-06d38c85e9e6447b9907e7a7bc636a80
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173704B2

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