Benzoyl Peroxide → 3-Fluoro-4-morpholin-4-ylmethylphenylamine

HRID 254938

Reaction equation

HRID 254938 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:11].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:11][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8083MorpholineHCID 67184N-bromobutanimideHCID 740252-Fluoro-4-nitrotoluene

Product 1

HCID 219550133-Fluoro-4-morpholin-4-ylmethylphenylamineYield 30%

Reagents, catalysts & solvents 1

HCID 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 filtered and concentrated. The residue was dissolved in THF (50 mL) and morpholine (1.9 g, 22 mmol) was added to this solution. The mixture was stirred at ambient temperature for 1 hour, and then filtered. The filtrate was evaporated. The title compound was isolated by column chromatography in an amount of 710 mg (30% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. customirradiated with light (100 W bulb) for 4 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in THF (50 mL)
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9876c79d99d34f47a247b5c338f69988
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Linked notes

Loading…