5-Chlorovaleryl chloride → 5-Chloro-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-1-pentanone

HRID 722938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722938
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:21])([F:20])[C:7]([N:9]1[CH2:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[CH2:11][CH2:10]1)=[O:8].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>ClCCCl>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([C:18]1[CH:17]=[CH:16][C:13]2[CH2:14][CH2:15][N:9]([C:7](=[O:8])[C:6]([F:5])([F:20])[F:21])[CH2:10][CH2:11][C:12]=2[CH:19]=1)=[O:28]

Komponenten

5

Edukt 3

HCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Produkt 1

HCID 218873015-Chloro-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-1-pentanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (17 g, 130 mmol) was added by portions to a solution of 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (15.0 g) and 5-chlorovaleryl chloride (8.8 ml) in 1,2-dichloroethane (40 ml) under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was poured into ice (500 g), extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was crystallized from ethanol-diethyl ether to give a pale yellow solid (15.2 g). Further recrystallization from ethanol-diethylether afforded colorless crystals (13.2 g) as the title compound.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was crystallized from ethanol-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-049ee60c4c134ce78c3c804f230f260d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138533B2

Notizen zur Reaktion

Wird geladen…