Morpholine → 4-(3-Nitrophenyl)morpholine

HRID 1825646Notes

Reaction equation

HRID 1825646 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C(#N)C>[N+:8]([C:4]1[CH:3]=[C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 98231-Fluoro-3-nitrobenzene

Product 1

HCID 12532734-(3-Nitrophenyl)morpholineYield 24.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Fluoronitrobenzene (10 g, 71 mmol) was dissolved in acetonitrile (100 mL). Morpholine (30 mL, 350 mmol) was added and the mixture was reacted 18 h at 150° C./80 psi in a pressure reactor. The reaction was cooled to room temperature, concentrated under vacuum and 5 g of the total mixture was purified by column chromatography on silica eluted with CH2Cl2. The product (3.6 g) was isolated as a bright yellow oil.

Workup

  1. customthe mixture was reacted 18 h at 150° C./80 psi in a pressure reactor
  2. concentrationconcentrated under vacuum and 5 g of the total mixture
  3. customwas purified by column chromatography on silica
  4. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-e1d09fc95645438abd0852b5375bfd0b
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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