p-Fluoronitrobenzene → HCID 7062386, compound

HRID 1441351Notes

Reaction equation

HRID 1441351 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[O:17][C@@H:16]([CH3:18])[CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][C@H:16]1[CH2:15][N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:13][C@@H:12]([CH3:11])[O:17]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 7062386HCID 7062386, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Fluoro-4-nitrobenzene (4.9 g, 34.75 mmol) was added to cis-2,6-dimethylmorpholine (44.4 g, 38.26 mmol) and anhydrous potassium carbonate (2.5 g, 18.12 mmol) in acetonitrile (50 ml). The reaction was heated under reflux for 19 hours, cooled, filtered and the solid washed with acetonitrile. Evaporation of the filtrate gave the title compound as a yellow solid. (8.1 g, 99%) NMR (CDCl3) 1.28 (d, 6H), 2.61 (t, 2H), 3.66 (td, 2H), 3.76 (m, 2H), 6.82 (d, 2H), 8.13 (d, 2H); m/z 237.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 19 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe solid washed with acetonitrile
  6. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-4175104d39ea46f48da2c81348b9dfe5
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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