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The Synthesis of N-(3-Methoxybenzyl)-N-methyl-3-methoxy-4,5-methylene-dioxyphenethylamine. (1948)

The Synthesis of N-(3-Methoxybenzyl)-N-methyl-3-methoxy-4,5-methylene-dioxyphenethylamine. (1948)

  1. staples
    Surrey, A. R.
    Journal of the American Chemical Society, 70(9), 2887-2890. doi: 10.1021/ja01189a016.

    The synthesis of N-(3-methoxybenzyl)-N-methyl-3-methoxy-4,5-methylenedioxyphenethylamine (I) was undertaken to determine its identity with α-fagarine, an alkaloid from the plant Fagara coco. A comparison of physical data has shown I to be different from α-fagarine, thus confirming the results recently reported by Surrey3 and by Redemann, Wisegarver and Icke. Inasmuch as our synthesis of 3-methoxy-4,5-methylenedioxyphenethylamine (II) is novel and more direct than those previously reported, we wish to describe it as well as certain other unreported experimental data involved in the synthesis of I. The synthesis of II by the rhodanine method of Gränacher has been carried out also. Since it nearly duplicates the work of Redemann and co-workers, only where variations occur in the physical data obtained for the compounds prepared in this synthesis, are such differences indicated in the experimental section.

    As shown in the accompanying flow sheet, the starting material used was myristicinaldehyde which was obtained in 51% yields by the oxidation of isomyristicin using a modification of the method of Milas. The required isomyristicin was obtained from the isomerization of myristicin by ethanolic potassium hydroxide. A fractionation of heavy oil of nutmeg provided the myristicin.

    Myristicinaldehyde was converted to the corresponding nitrostyrene by means of nitromethane. Reduction by lithium aluminum hydrides provided a ready synthesis of III. The N-(3-methoxybenzyl)-3-methoxy-4,5-methylenedioxyphenethylamine (111) was prepared by catalytic hydrogenation of the Schiff base from II and 3-methoxybenzaldehyde. Methylation by the lithium aluminum hydride reduction of the formyl derivative of III resulted in the formation of I in good yield. The isolation and characterization of I and III as free bases, as well as the above mentioned Schiff base, are described.