Morpholine → 4-(2-Fluoro-4-nitrophenyl)morpholine

HRID 245305Notes

Reaction equation

HRID 245305 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholineYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,4-difluoro-nitrobenzene (100 g, 0.63 mol) was added dropwise to morpholine (60 g, 0.69 mol) and triethylamine (70 g, 0.69 mol) in ethyl acetate (300 mL) within 1 hour while maintaining the temperature below 50° C. The mixture is stirred at 45˜50° C. for 10 hours until the completion of the reaction. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate, filtered, dried, to provide 138 g of yellow solid in 97% yield.

Workup

  1. temperaturewhile maintaining the temperature below 50° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-dab7557d28b94e99a376ef3f67a047bb
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Reaction notes

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