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

HRID 2212840Notes

Reaction equation

HRID 2212840 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].BrN1C(=O)CCC1=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 740252-Fluoro-4-nitrotoluene

Product 1

HCID 219550274-(2-Fluoro-4-nitrobenzyl)morpholineYield 55%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Fluoro-4-nitrotoluene (1.55 g, 10 mmol), N-bromosuccinimide (1.82 g, 10 mmol), and benzoyl peroxide (0.1 g, 0.4 mmol) were dissolved in CCl4 (50 mL). The mixture was heated at reflux, and irradiated with light (100 W bulb) for 4 hours. The reaction mixture was then filtered and concentrated. The residue was dissolved in THF (50 mL). Morpholine (1.91 g, 22 mmol) was added to it. The mixture was stirred at ambient temperature for 1 hour and then filtered. The filtrate was evaporated. The bright orange residue was purified by column chromatography eluted with hexane:ethyl acetate, 10:1 to provide 4-(2-fluoro-4-nitrobenzyl)morpholine (1.32 g, 5.5 mmol, yield 55%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. customirradiated with light (100 W bulb) for 4 hours
  4. filtrationThe reaction mixture was then filtered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in THF (50 mL)
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customThe bright orange residue was purified by column chromatography
  10. washeluted with hexane

Sources & evidence

ORD record
ord-d70c75d40ce04133bad7692f1137d75b
Source dataset
uspto-grants-2006_09
Patent number
US07105503B2

Reaction notes

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