1-Morpholinocyclopentene → HCID 22052524, compound

HRID 1937016Notes

Reaction equation

HRID 1937016 reaction equation
O1CCN([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)CC1.[Br:12][C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1.CCCCCC.C(OCC)(=[O:30])C>C(Cl)(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([CH:7]2[CH2:8][CH2:9][CH2:10][C:11]2=[O:30])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 702941-MorpholinocyclopenteneHCID 1410013-Bromophenyl isocyanateHCID 21226206Ethyl acetate hexane

Product 1

HCID 22052524HCID 22052524, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Morpholino-1-cyclopentene (15.2 ml, 101 mmol) is carefully added in drops to a solution of 3-bromophenylisocyanate (20.0 g, 101 mmol) in chloroform (100 ml). The batch is refluxed for 15 minutes and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yielded 25.0 g (88.6 mmol) of cyclopentan-2-one-1-carboxylic acid-(3-bromophenyl)amide. The latter are mixed with concentrated sulfuric acid (83 ml) and stirred for 30 minutes at 90° C. After cooling to room temperature, the batch is poured onto 600 g of ice, the precipitated solid is suctioned off and recrystallized from ethanol: 17.0 g of product.

Workup

  1. temperatureThe batch is refluxed for 15 minutes
  2. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7e59db0c9f53452fb73c652c1603eeb5
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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