Synthesis of Tramadol and Analogous

Tramadol is a drug with analgesic properties. This compoundand five of its analogous were synthesized: N-demethyl (M2),O-demethyl (M1), O-ethyl-O-demethyl, O-benzyl-O-demethyl and Nbenzyl-N-demethyl. All compounds were prepared as theirhydrochlorides and as racemic mixtures. The synthesis started wi...

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Detalles Bibliográficos
Autores: Rocío Patiño, Cuauhtémoc Alvarado, Ángel Guzmán, Eduardo Díaz
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:México
Institución:Universidad Nacional Autónoma de México
Repositorio:Redalyc-UNAM
OAI Identifier:oai:redalyc.org:47549406
Acceso en línea:https://www.redalyc.org/articulo.oa?id=47549406
Access Level:acceso abierto
Palabra clave:Química
opioids
Tramadol
analgesics
nonsteroids
antiinflammatories
Descripción
Sumario:Tramadol is a drug with analgesic properties. This compoundand five of its analogous were synthesized: N-demethyl (M2),O-demethyl (M1), O-ethyl-O-demethyl, O-benzyl-O-demethyl and Nbenzyl-N-demethyl. All compounds were prepared as theirhydrochlorides and as racemic mixtures. The synthesis started withthe aminoketones; 2-(N-benzyl, N-methyl)aminomethyl cyclohexanoneand 2-dimethylaminomethyl cyclohexanone, prepared by meansof a Mannich reaction of cyclohexanone, paraformaldehyde and thecorresponding amino hydrochloride. The aminoketones were coupledwith the organolithium compounds derived from the corresponding 3-bromoalkoxybenzenes.