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

HRID 1441353Notes

Reaction equation

HRID 1441353 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

1,2-Difluoro-4-nitrobenzene (8.0 g, 50 mmol) was added to morpholine (4.85 g, 55.7 mmol) and anhydrous potassium carbonate (3.85 g, 27.9 mmol) in acetonitrile (75 ml). The reaction was heated at 85° C. for 3 hours, cooled, filtered and the solid washed with EtOAc (50 ml). Evaporation of the filtrate, trituration with isohexane and filtration gave the title compound as a solid (11.2 g, 98%). NMR (CDCl3): 3.28 (t, 4H), 3.88 (t, 4H), 6.92 (t, 1H), 7.92 (dd, 1H), 8.00 (m, 1H); m/z 227.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washthe solid washed with EtOAc (50 ml)
  4. customEvaporation of the filtrate, trituration
  5. filtrationwith isohexane and filtration

Sources & evidence

ORD record
ord-f87666db7c21415e89da5bf8d923681f
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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