Hydrochloric Acid → 2-chloro-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]ethanone

HRID 1668371Notes

Reaction equation

HRID 1668371 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[F:10][C:11]([F:26])([F:25])[C:12]([N:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[CH2:16][CH2:15]1)=[O:13].Cl>ClC(Cl)C>[Cl:1][CH2:2][C:3]([C:23]1[CH:22]=[CH:21][C:18]2[CH2:19][CH2:20][N:14]([C:12](=[O:13])[C:11]([F:25])([F:10])[F:26])[CH2:15][CH2:16][C:17]=2[CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 592398392-chloro-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]ethanoneYield 88.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of chloroacetyl chloride (7.0 g) in dichloroethane (50 ml) was added aluminum chloride (8.2 g) at room temperature, and then a solution of 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (3.0 g) in dichloroethane (50 ml) was added. The obtained mixture was stirred at room temperature for 3 hr, and poured into ice-cooled 1N is hydrochloric acid (80 ml). Dichloroethane was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio) to give the title compound (3.5 g) as a colorless powder.

Workup

  1. additionpoured into ice-
  2. temperaturecooled 1N
  3. customDichloroethane was evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate-hexane (1:1, volume ratio)

Sources & evidence

ORD record
ord-9cd46f5073ea4028a8fc38a2f6660e61
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

Loading…