FIELD: chemistry.
SUBSTANCE: invention relates to an improved process for the preparation of alverine [3-phenyl-N-(3-phenylpropyl)-N-ethyl-propan-1-amine]. Alverine has the properties of a smooth muscle relaxant and is used as an antispasmodic for the discoloration of bile ducts, pilorospasm, spastic colitis and disinorrhea, as well as in other areas of organic chemistry. Method is that ethylamine hydrochloride is allylated with (E)-1,3-dichloropropene. This way the bis[(2E)-3-chloroprop-2-en-1-yl]ethanamine is obtained, which is subjected to Fe(acac)3-catalyzed double cross-coupling with phenylmagnesiumbromide in tetrahydrofuran under an inert gas atmosphere, followed by hydrogenation of the resulting bis[(2E)-3-phenylprop-2-en-1-yl]ethanamine in the presence of catalytic amounts of Pd/C.
EFFECT: method makes it possible to obtain products in high yield using a low-toxicity Fe catalyst [Fe(acac)3] and more accessible starting reagents.
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Authors
Dates
2018-06-07—Published
2017-09-12—Filed