Water → 4-(2-Fluoro-4-nitrophenyl)morpholine

HRID 2207057Notes

Reaction equation

HRID 2207057 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C.O>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholineYield 94.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
27.5 °C

Procedure

3,4-difluoro nitrobenzene (100 gr) is slowly added to a mixture of morpholine (76.6 gr), triethylamine (23 ml) and in presence of acetonitrile solvent (115 ml) at 40-50° C. Reaction mass is heated for 6 hrs at reflux temperature, cooled to 25-30° C. Then water (600 ml) is added slowly to the reaction mass and then cooled to 0-5° C. The reaction mixture is stirred for 1 hr. The solid is filtered to give 134 gr of 3-fluoro-4-morpholinyl nitrobenzene.

Workup

  1. customReaction mass
  2. temperatureis heated for 6 hrs
  3. temperatureat reflux temperature
  4. temperaturecooled to 0-5° C
  5. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-3f9442bbedaa49c7a228f2be931bd244
Source dataset
uspto-grants-2016_06
Patent number
US09376407B2

Reaction notes

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