METHOD OF PRODUCING 2-(AMINOALKYL)-3-(AMINOPHENYL)BICYCLO[2,2,1]HEPTANES Russian patent published in 2013 - IPC C07C209/36 C07C211/44 

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method of producing 2-(aminoalkyl)-3-(aminophenyl)bicyclo[2.2.1]heptanes of formula (I). Mono- and diamines containing a bicyclic moiety can be used in medicine as an agent for medicinal preparations having thymoleptic, tonic action, are used in treating cocaine addiction and can also be of interest as potential monomers for polycondensation polymers. The method of producing said compounds involves reacting a nitrocinnamic aldehyde (dienophile) with cyclopentadiene to obtain a corresponding 3-(nitrophenyl)bicyclo[2.2.1]hept-5-ene-2-carbaldehyde, which is condensed with proton-mobile compounds, for example with hydroxyl amine, nitromethane or cyanoacetic acid. The corresponding 2-substituted-3-phenylbicyclo[2.2.1]hept-5-ene derivative is obtained, which is reduced with active hydrogen obtained by reacting a nickel-aluminium alloy with potassium hydroxide to obtain a compound of general formula (I) where n=1, 2, 3.

EFFECT: use of the disclosed method as a source compound of nitrocinnamic aldehyde enables to obtain a product with high degree of purity and output, simplifies the process and improves technological effectiveness thereof, reduces reactivity of compounds in Diels-Alder reactions, enables to obtain not only aminomethyl compounds, but also other aminoalkyl compounds using a simpler process.

1 dwg, 8 ex