Morpholine → 4-(3,5-Difluoro-2-nitro-phenyl)-morpholine

HRID 1820125Notes

Reaction equation

HRID 1820125 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CS(C)=O>[F:9][C:4]1[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 672635064-(3,5-Difluoro-2-nitro-phenyl)-morpholineYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
10 °C

Procedure

2,4,6-Trifluoronitrobenzene (4.95 g) and potassium carbonate (4.63 g) were mixed in dry dimethyl sulfoxide (40 mL) and cooled to 10° C. under argon. Morpholine (2.56 mL) was added and the reaction mixture was allowed to warm to 25° C. and stirred under argon for 16 hours. The reaction mixture was concentrated in vacuo, brine (50 mL) was added and the product was extracted with ethyl acetate (3×50 mL), the combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography to furnish 3.69 g (54% yield) of the title compound as a yellow oil.

Workup

  1. temperatureto warm to 25° C.
  2. concentrationThe reaction mixture was concentrated in vacuo, brine (50 mL)
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate (3×50 mL)
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-434fdd0d82d64d058a959e554d2a3331
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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