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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X


ALVARADO, Cuauhtémoc; GUZMAN, Ángel; DIAZ, Eduardo  and  PATINO, Rocío. Synthesis of Tramadol and Analogous. J. Mex. Chem. Soc [online]. 2005, vol.49, n.4, pp.324-327. ISSN 1870-249X.

Tramadol is a drug with analgesic properties. This compound and five of its analogous were synthesized: N-demethyl (M2), O-demethyl (M1), O-ethyl-O-demethyl, O-benzyl-O-demethyl and N-benzyl-N-demethyl. All compounds were prepared as their hydrochlorides and as racemic mixtures. The synthesis started with the aminoketones; 2-(N-benzyl, N-methyl)aminomethyl cyclohexa-none and 2-dimethylaminomethyl cyclohexanone, prepared by means of a Mannich reaction of cyclohexanone, paraformaldehyde and the corresponding amino hydrochloride. The aminoketones were coupled with the organolithium compounds derived from the corresponding 3-bromoalkoxybenzenes.

Keywords : Tramadol; antiinflammatories; analgesics; nonsteroids; opioids.

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