1-Morpholinocyclopentene → HCID 22052524, compound

HRID 1831731Notes

Reaction equation

HRID 1831731 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

15.2 ml (101 mmol) of 1-morpholino-1-cyclopentene is carefully added in drops to a solution of 20.0 g (101 mmol) of 3-bromophenylisocyanate in 100 ml of chloroform. 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 is mixed with 83 ml of concentrated sulfuric acid 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-c9217b53961c4eb0895e52cd29fcffff
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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