Hydrochloric Acid → HCID 58494928, compound

HRID 516243Notes

Reaction equation

HRID 516243 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].C[O:10][C:11]1[CH:28]=[CH:27][C:14]2[CH:15]([CH3:26])[CH2:16][N:17]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:18][CH2:19][C:13]=2[CH:12]=1.Cl>ClCCl.C(Cl)(Cl)Cl.O>[OH:7][C:5]1[C:28]([C:11](=[O:10])[CH3:12])=[CH:27][C:14]2[CH:15]([CH3:26])[CH2:16][N:17]([C:20](=[O:25])[C:21]([F:24])([F:22])[F:23])[CH2:18][CH2:19][C:13]=2[CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22292800HCID 22292800, compound

Product 1

HCID 58494928HCID 58494928, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixed liquid of 9.3 g of aluminum chloride in 30 ml of dichloromethane was added dropwise 1.6 ml of acetyl chloride under ice-cooling, followed by stirring. Then, a solution of 5 g of 7-methoxy-1-methyl-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine in 70 ml of dichloromethane was added thereto, followed by stirring for 13 hours while slowly elevating the temperature to room temperature. The reaction mixture was ice-cooled, and 30 ml of 1 M hydrochloric acid was added dropwise thereto, followed by addition of water and extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (elution solvent: HEX-EtOAc) to obtain 5.137 g of 1-[8-hydroxy-5-methyl-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-yl]ethanone as a pale brown solid.

Workup

  1. temperaturecooling
  2. stirringby stirring for 13 hours
  3. customto room temperature
  4. temperaturecooled
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-df865fa8d16f49bd9261610e6df4336f
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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