1-Morpholinocyclopentene → HCID 22462443, compound

HRID 1937007Notes

Reaction equation

HRID 1937007 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.O1CCN([C:17]2[CH2:21][CH2:20][CH2:19][CH:18]=2)CC1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9](=[O:10])[C:18]3[CH2:19][CH2:20][CH2:21][C:17]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 702941-MorpholinocyclopenteneHCID 709554-Fluorophenyl isocyanate

Product 1

HCID 22462443HCID 22462443, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-fluorophenylisocyanate (5.0 g, 36.5 mmol) in chloroform (25 ml) is mixed with 1-morpholino-1-cyclopentene (5.5 ml, 36.5 mmol) and refluxed for 15 minutes. The batch is concentrated by evaporation and purified by column chromatography (SiO2) with ethyl acetate-hexane: 7.6 g (94%) of cyclopentanone-2-carboxylic acid-(4-fluorophenyl)amide, 1H-NMR (DSC842). The amide is stirred in concentrated sulfuric acid (30 ml) for 30 minutes at 100° C. The batch is poured onto ice water and filtered. The filter residue is recrystallized from ethanol: 2.02 g (29%) of product.

Workup

  1. temperaturerefluxed for 15 minutes
  2. concentrationThe batch is concentrated by evaporation
  3. custompurified by column chromatography (SiO2) with ethyl acetate-hexane
  4. additionThe batch is poured onto ice water
  5. filtrationfiltered
  6. customThe filter residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-aac41142315c45f4831b0a2bc5bd9e81
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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