1,2,3-Trifluoro-5-nitrobenzene → 3,5-Difluoro-4(7,7-ethylenedioxy-5-azaspiro[2,4]heptan-5-yl)nitrobenzen

HRID 1920094Notes

Reaction equation

HRID 1920094 reaction equation
[CH2:1]1[CH2:11][O:10][C:3]2([C:7]3([CH2:9][CH2:8]3)[CH2:6][NH:5][CH2:4]2)[O:2]1.[F:12][C:13]1[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=[C:17]([F:20])[C:18]=1F>C(#N)C>[F:12][C:13]1[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=[C:17]([F:20])[C:18]=1[N:5]1[CH2:4][C:3]2([O:2][CH2:1][CH2:11][O:10]2)[C:7]2([CH2:8][CH2:9]2)[CH2:6]1

Participants

4

Reactant 2

HCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 224172225,8-Dioxa-10-azadispiro[2.0.4.3]undecane

Product 1

HCID 592348533,5-Difluoro-4(7,7-ethylenedioxy-5-azaspiro[2,4]heptan-5-yl)nitrobenzenYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 7,7-ethylenedioxy-5-azaspiro[2,4]heptane in acetonitrile (50 mL) was dropwise added 3,4,5-trifluoronitrobenzene (5.3 g, 31.6 mmol) and the reaction mixture was refluxed for 3 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and the solvent was removed therefrom by vacuum distillation. It was diluted with ethyl acetate and water, and the organic phase thus formed was dried over magnesium sulfate. The residue was filtered, concentrated in a vacuum, and purified through column chromatography (n-hexane/ethyl acetate=4:1) to afford the target compound (3.5 g, yield 66%).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customAfter the reaction was terminated
  3. customthe solvent was removed
  4. distillationby vacuum distillation
  5. additionIt was diluted with ethyl acetate and water
  6. customthe organic phase thus formed
  7. dry with materialwas dried over magnesium sulfate
  8. filtrationThe residue was filtered
  9. concentrationconcentrated in a vacuum
  10. custompurified through column chromatography (n-hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-273f62f5b29341afa7051f47f67f0041
Source dataset
uspto-grants-2012_05
Patent number
US08168797B2

Reaction notes

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