Morpholine → 4-(3-Iodo-5-nitrophenyl)morpholine

HRID 2207350Notes

Reaction equation

HRID 2207350 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([I:17])[CH:9]=1>CS(C)=O.CCOCC.C(OCC)(=O)C>[I:17][C:10]1[CH:9]=[C:8]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 2590861-Fluoro-3-iodo-5-nitrobenzene

Product 1

HCID 584563064-(3-Iodo-5-nitrophenyl)morpholine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Morpholine (2.53 mL, 28.1 mmol) was added to a solution of 1-fluoro-3-iodo-5-nitrobenzene (3 g, 11.2 mmol) in DMSO (22.5 mL) under nitrogen. The reaction was heated at 120° C. for 2 hours, then cooled to room temperature and diluted with a mixture of ether and ethyl acetate. The organic layer was washed with water (2×) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexanes) to afford 4-(3-iodo-5-nitrophenyl)morpholine as deep yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water (2×)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-eee7bdcc65cc492394fb8271d13cb598
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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