HCID 57656425, compound → 2,2,2-Trifluoro-1-(6-fluoro-1,2,4,5-tetrahydro-9-methoxy-3H-3-benzazepin-3-yl)ethanone

HRID 911217Notes

Reaction equation

HRID 911217 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][C:6]=2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.[H][H]>CCOC(C)=O.C(O)C.[Pd]>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 57656425HCID 57656425, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 576562002,2,2-Trifluoro-1-(6-fluoro-1,2,4,5-tetrahydro-9-methoxy-3H-3-benzazepin-3-yl)ethanoneYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

Dissolve 9-fluoro-6-methoxy-3-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-benzo[d]azepine (9.4 g, 32.4 mmol) with 10% Pd/C (dry basis, Degussa type, 1.4 g, 0.65 mmol) in EtOAc/ethanol (1:1, 200 mL) and stir at ambient temperature under a balloon of hydrogen for 4.5 h. Filter the mixture through a pad of silica gel and evaporate the filtrate to obtain the desired intermediate (8.6 g, 91%). MS (ES+) m/z: 292 (M+H)+.

Workup

  1. filtrationFilter the mixture through a pad of silica gel
  2. customevaporate the filtrate

Sources & evidence

ORD record
ord-135ad9069abb4cbcb8f5ed69e9ebe809
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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