Morpholine → 4-Morpholino-3-(trifluoromethyl)benzonitrile

HRID 1465022Notes

Reaction equation

HRID 1465022 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>CC(N(C)C)=O.C(OCC)(=O)C>[O:17]1[CH2:18][CH2:19][N:14]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

Product 1

HCID 595565444-Morpholino-3-(trifluoromethyl)benzonitrileYield 77.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

4-Fluoro-3-(trifluoromethyl)benzonitrile (2.0 g, 10.58 mmol) was dissolved in dimethyl acetamide (35 mL), morpholine (2.88 mL, 31.73 mmol) was added thereto, and the mixture was subjected to a reaction at 145° C. for 19 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and the organic layer was washed with an aqueous sodium hydrogen carbonate solution (50 mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was crystallized with ethyl acetate (10 mL) and n-hexane (80 mL) to obtain the title compound as a brown solid (2.1 g).

Workup

  1. customthe mixture was subjected to a reaction at 145° C. for 19 hours
  2. washthe organic layer was washed with an aqueous sodium hydrogen carbonate solution (50 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried with sodium sulfate
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe concentrated mixture was crystallized with ethyl acetate (10 mL) and n-hexane (80 mL)

Sources & evidence

ORD record
ord-c50416b3835a46f1b0d6abacb2b605f1
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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