GC-MS and LC of Addition Products Formed from the Reaction of ...

Published: Journal of Chromatographic Science, Volume 33, Number 5, May 1995, pp. 256-262.

GC–MS and LC of Addition Products Formed from the Reaction of Allylbenzene and Related Arylpropenes with Acetonitrile and Sulfuric Acid
F. Taylor Noggle, C. Randall Clark, and Jack DeRuiter

The synthesis of amphetamine and related compounds from several arylpropenes is investigated using gas chromatography–mass spectrometry and liquid chromatography. Treatment of allylbenzene with acetonitrile and sulfuric acid yields a mixture of 1-phenyl-2-acetamidopropane and 1-phenyl-1-acetamidopropane. Hydrolysis of this product mixture gives the corresponding propanamines, amphetamine and 1-phenyl-1-propanamine. When the isomeric compound trans-b-methylstyrene is subjected to this reaction sequence, a single amine product, 1-phenyl-1-propanamine, is obtained. Treatment of the isomeric 3,4-methylenedioxyphenylpropenes (safrole and isosafrole) with acetonitrile and sulfuric acid followed by acid hydrolysis did not result in the formation of 3,4-methylenedioxyamphetamine (MDA). Safrole yields a dihydroisoquinoline derivative, whereas isosafrole gives simple dimers under these reaction conditions. The differences in the products obtained in these studies appear to be determined by differences in the electronic nature of the starting arylpropenes.

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