Morpholine → 4-(3-Fluoro-4-nitrophenyl)morpholine

HRID 968355Notes

Reaction equation

HRID 968355 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=1.[F:1][C:2]1[CH:7]=[C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 679672,4-Difluoronitrobenzene

Product 2

HCID 222807594-(3-Fluoro-4-nitrophenyl)morpholineHCID 22280782HCID 22280782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-difluoronitrobenzene (10.0 mL) and morpholine (17.4 mL) in THF (100 mL) was stirred at RT under N2 for 2 h. The solvent was removed and the residue was partitioned between EtOAc and water. The organic layer was washed brine, dried over MgSO4, and concentrated. The resulting solid was purified by chromatography on silica gel with 20-50% EtOAc in hexane to give 18.1 g of 4-fluoro-2-morpholinonitrobenzene and 1.81 g of 2-fluoro-4-morpholinonitrobenzene. ESI mass spectrum z (rel. intensity) 227.1 (M+H, 100).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting solid was purified by chromatography on silica gel with 20-50% EtOAc in hexane

Sources & evidence

ORD record
ord-0fc25e741c634cadb4c22207c1d5ea39
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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