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N-Methyltyramine and N,O-Dimethyltyramine Synthesis via Intermediate 4-Methoxyphenyl-N-methyltioacetamide.
* 1 , 2 , 2
1  Scientific-Research Phototechnical Institute on Slavich Company (NIFTI-Slavich); Mendeleev sq. 2, Pereslavl-Zalesskii, Yaroslavl region, 152140, Russian Federation.
2  All-Russian Institute of Medicinal and Aromatic Plants (VILAR); Grina str., 7, Moscow, 113628, Russian Federation

Abstract: N-Methyltyramine and its alkyl or benzyl ethers are common intermediate products in the syntheses of narwedine, and galanthamine alkaloids [1-8]. They are usually produced from the corresponding arylacetamides by lithium aluminium hydride reduction. In order to avoid application of inflammable lithium aluminium hydride bulgarian scientists have transformed arylacetamide to arylthioacetamide with phosphorus (V) sulfide with following reduction of arylthioacetamide with complex sodium borohydride - nickel or cobalt chloride agents [7, 8]. Here we present a new short way route to N-methyltyramine and its ethers via the corresponding aryl-N-methylthioacetamides, shown at the scheme 1 at the example of N-methyltyramine and N,O-dimethyltyramine synthesis.
Keywords: galanthamine synthesis half-products, N-methyltyramine, N-methyltyramine ethers, N,O-dimethyltyramine, arylthioacetamide, Willgerodt-Kindler reaction