Enamine chemistry. Part XVI. Reaction of αβ-unsaturated acid chlorides with 1,4-dimorpholinocyclohexa-1,3-diene. Synthesis of 7-morpholino- and 4,7-dimorpholino-indan-1-ones

Abstract

The reaction of acryloyl chloride with 1,4-dimorpholinocyclohexa-1,3-diene has been shown to give 7-morpholino-indan-1-one. In a similar way methacryloyl, crotonoyl, and cinnamoyl chlorides gave the corresponding 2-methyl-, 3-methyl-, and 3-phenyl-7-morpholinoindan-1-one, respectively, and β-chloroacryloyl chloride gave 4,7-di-morpholinoindan-1 -one. Yields were low owing to competing formation of 1,4-dimorpholinobenzene and the corresponding αβ-unsaturated acid morpholide.