HENRY CONDENSATION AT HIGH-PRESSURES .1. SYNTHESIS OF 1-(3,4-METHYLENEDIOXYPHENYL)-2-NITRO-1-BUTENE AND AN IMPROVED SYNTHESIS OF 1-(3,4-METHYLENE-DIOXYPHENYL)-2-METHYLAMINOBUTANE

The hitherto inaccessible nitroolefin (VII), which is the most convenient intermediate for the synthesis of the psychotropic amine (VIII), has been obtained by the direct condensation at high pressures (up to 1500 MPa) of piperonal (V) with 1-nitropropane (VI). The structure of (VII) was confirmed by direct synthesis from pyrocatechol (X). The amine (VIII) was obtained in three steps from (VII). This synthesis of (VIII) is shorter than that previously reported. © 1990 Plenum Publishing Corporation.