Benzoyl Peroxide → HCID 21069832, compound

HRID 348123Notes

Reaction equation

HRID 348123 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])[CH:7]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:16][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8]([N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)=[O:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21069934HCID 21069934, compound

Product 1

HCID 21069832HCID 21069832, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of intermediate 41, (5-fluoro-2-methylphenyl)(morpholino)methanone, (2.1 g, 9.5 mmol) and N-bromosuccinimide (2.0 g, 11 mmol) in CCl4 (30 mL) was heated at reflux. To this mixture was added benzoylperoxide (242 mg, 1 mmol) and the mixture heated at reflux for 2 hrs. After cooling, the insoluble materials were filtered and the filtrate purified by column chromatography (SiO2, 0–10% ether in CH2Cl2) to give 1.1 g (Yield 38%) of the title compound as a clear oil: 1H NMR (300 MHz, CDCl3) δ ppm: 3.31 (2H, t, J=4.94 Hz) 3.55–4.02 (6H, m) 4.56 (2H, dd, J=128.81, 9.51 Hz) 6.89 (1 H, dd, J=8.23, 2.74 Hz) 6.96–7.12 (1H, m) 7.33–7.49 (1H, m); LC/MS m/z 302 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe mixture heated
  4. temperatureat reflux for 2 hrs
  5. temperatureAfter cooling
  6. filtrationthe insoluble materials were filtered
  7. customthe filtrate purified by column chromatography (SiO2, 0–10% ether in CH2Cl2)

Sources & evidence

ORD record
ord-5d77a43c90e645d8957608b45b650e5e
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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