Morpholine → 4-(2,6-Difluoro-4-nitrophenyl)morpholine

HRID 1950746Notes

Reaction equation

HRID 1950746 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[F:16][C:17]1[CH:18]=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=[C:21]([F:24])[C:22]=1F>CN1CCCC1=O.O.Cl>[F:16][C:17]1[CH:18]=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=[C:21]([F:24])[C:22]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 223856304-(2,6-Difluoro-4-nitrophenyl)morpholine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

5.10 mL morpholine are dissolved in 1 mL 1-methyl-2-pyrrolidon and combined with 14.99 mL N,N-diisopropylethylamine and 1.85 mL 3,4,5-trifluoronitrobenzene. The reaction mixture is stirred for 1 h at 110° C. After cooling the reaction mixture is diluted with 70 mL water and 15 mL concentrated aqueous HCl solution are added. The precipitate formed is filtered off, with water washed and dissolved with ethyl acetate. Then the solvent is eliminated in vacuo.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. additionare added
  3. customThe precipitate formed
  4. filtrationis filtered off, with water
  5. washwashed
  6. dissolutiondissolved with ethyl acetate

Sources & evidence

ORD record
ord-b6375a40d2604ebaa75529dc631e0ccd
Source dataset
uspto-grants-2013_03
Patent number
US08404674B2

Reaction notes

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