Morpholine → HCID 22280782, compound

HRID 132605Notes

Reaction equation

HRID 132605 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+]([O-])=O.FC1C=C(F)C=CC=1[N+:25]([O-:27])=[O:26].N1CCOCC1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:25]([O-:27])=[O:26])=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 679672,4-DifluoronitrobenzeneHCID 222807594-(3-Fluoro-4-nitrophenyl)morpholine

Product 1

HCID 22280782HCID 22280782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(3-Fluoro-4-nitrophenyl)morpholine: A solution of 2,4-difluoronitrobenzene (10.0 mL, 91 mmol) and morpholine (17.4 mL, 200 mmol) in THF (100 mL) was stirred at RT under nitrogen 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 SiO2 chromatography with 20-50% EtOAc in hexane to give 4-fluoro-2-morpholinonitrobenzene (18.1 g) and 55a (1.81 g, 8% yield); [M+H]+=227.10.

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 SiO2 chromatography with 20-50% EtOAc in hexane

Sources & evidence

ORD record
ord-6458e52c9cbc417da9da90c0499832cf
Source dataset
uspto-grants-2008_06
Patent number
US07388021B2

Reaction notes

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