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

HRID 56088

Reaction equation

HRID 56088 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN(CC)CC.[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CCOC(C)=O>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

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

Product 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholineYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of morpholine (12.04 g, 0.14 mol) and Et3N (13.97 g, 0.14 mol) in EtOAc was added 3,4-difluoronitrobenzene (20.0 g, 0.13 mol) dropwise in an ice bath. The reaction mixture was warmed to rt slowly, stirred at rt overnight, and then filtered. The filter cake was washed with water, dried in vacuo to obtain the 1st crop of product. The organic phase was separated from the filtrate, and the water phase was washed with EtOAc. The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo to obtain the 2nd crop of product. The solids of 1st crop and 2nd crop were combined to give the title compound as a yellow solid (28.0 g, 99%).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water
  3. customdried in vacuo
  4. customto obtain the 1st crop of product
  5. customThe organic phase was separated from the filtrate
  6. washthe water phase was washed with EtOAc
  7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto obtain the 2nd crop of product

Sources & evidence

ORD record
ord-50124155b9af4ad6bdae3bd136f7e5aa
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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