HCID 14257319, compound → HCID 15612105, compound

HRID 580404Notes

Reaction equation

HRID 580404 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][C:14]3[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:13]=3[NH:12][C:11](=[O:24])[CH:10]2[CH2:25][CH:26]=[CH2:27])=[CH:5][CH:4]=1>C(O)(=O)C.FC(F)(F)C(O)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][C:14]3[CH:16]=[C:17]([C:20]([F:21])([F:22])[F:23])[CH:18]=[CH:19][C:13]=3[NH:12][C:11](=[O:24])[CH:10]2[CH2:25][CH2:26][CH3:27])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 14257319HCID 14257319, compound

Product 1

HCID 15612105HCID 15612105, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1,3,4,5-Tetrahydro-4-(4-methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one (3.50 g; 9.32 mmole; see Example 5, Method II, part D) was dissolved in glacial acetic acid (100 ml) and trifluoroacetic acid (50 ml). Palladium on charcoal (0.71 g) was added to the degassed solution, and the mixture was placed on a Parr apparatus for four hours. The solution was then filtered through a pad of Celite and the Celite was rinsed several times with ethyl acetate. The concentrated mixture was vacuum dried yielding 3.53 g of the title compound as a solid.

Workup

  1. filtrationThe solution was then filtered through a pad of Celite
  2. washthe Celite was rinsed several times with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-bbca58b6634a4752ba7d8ff66a86d200
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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