Morpholine → Morpholine, 4-(2-chloro-4-nitrophenyl)-

HRID 56227

Reaction equation

HRID 56227 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1F.CCN(CC)CC>CN(C=O)C>[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 108711Morpholine, 4-(2-chloro-4-nitrophenyl)-Yield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of morpholine (1.1 mL, 12.6 mmol) in DMF (30 mL) were added 2-chloro-1-fluoro-4-nitrobenzene (1.76 g, 10.0 mmol) and Et3N (4.2 mL, 30.1 mmol) with stirring and the mixture was stirred at rt overnight. The mixture was then filtered and the organic phase was poured into 150 mL of DCM, washed with water (150 mL×3) and brine (150 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1) to give the title compound as a yellow solid (1.53 g, 63%).

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. filtrationThe mixture was then filtered
  3. additionthe organic phase was poured into 150 mL of DCM
  4. washwashed with water (150 mL×3) and brine (150 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1)

Sources & evidence

ORD record
ord-f4072d50c2dc4c7bb60dd7a9c543384b
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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