Water → HCID 86658948, compound

HRID 516251Notes

Reaction equation

HRID 516251 reaction equation
Br[C:2]1[C:3]2[CH2:20][CH2:19][N:18]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:17][CH2:16][C:4]=2[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][O:14][CH3:15])[CH2:9][CH2:8][CH2:7]2.[F:27][C:28]([F:33])([F:32])C([O-])=O.[Na+].CN1CCCC1=O.O>[Cu](I)I.C(OCC)(=O)C>[F:25][C:22]([F:24])([F:23])[C:21]([N:18]1[CH2:19][CH2:20][C:3]2[C:2]([C:28]([F:33])([F:32])[F:27])=[C:11]3[C:6]([CH2:7][CH2:8][CH2:9][N:10]3[CH2:12][CH2:13][O:14][CH3:15])=[CH:5][C:4]=2[CH2:16][CH2:17]1)=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 86658949HCID 86658949, compound

Product 1

HCID 86658948HCID 86658948, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

1.1946 g of 1-[11-bromo-1-(2-methoxyethyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-yl]-2,2,2-trifluoroethanone, 2.2395 g of sodium trifluoroacetate, and 1.568 g of copper iodide were added to 24 ml of N-methylpyrrolidone under an argon atmosphere, followed by stirring at 170° C. for 18 hours. To the reaction mixture were added water and ethyl acetate, and filtered through celite was performed. The filtrate was subjected to liquid separation, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: Hex-AcOEt) to obtain 239 mg of 2,2,2-trifluoro-1-[1-(2-methoxyethyl)-11-(trifluoromethyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-yl]ethanone as a pale yellow solid.

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was subjected to liquid separation
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: Hex-AcOEt)

Sources & evidence

ORD record
ord-e5e141d72c6a4746820fe518406f0a05
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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