1-Morpholinocyclopentene → HCID 22052524, compound

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Reaction Steps

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.

Provenance & Evidence