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

HRID 719793Notes

Reaction equation

HRID 719793 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-627a338d82fa40b5804eeb75f73f80af
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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