143603-44-5Relevant academic research and scientific papers
Synthesis of Isothiocyanato-1-thienyl)cyclohexyl>piperidines, Potential Irreversible Ligands at the Dopamine Re-uptake Site
Costa, Brian de,George, Clifford,Dominguez, Celia
, p. 1671 - 1680 (2007/10/02)
Isomeric isothiocyanate derivatives 2-7 of the potent dopamine re-uptake (DA) inhibitor 1-thienyl)cyclohexyl>piperidine (BTCP 1) have been synthesized as potential irreversible ligands for this site.NaNO2-CF3CO2H provided a mild procedure for mononitration of the benzothienyl ring of 1 as a route to aryl isothiocyanates 5-7.Novel methodology, utilizing 3,3-ethylenedioxypentane-1,5-diol dimethanesulfonate ester is described for the synthesis of piperidone 13, a precursor for 4-isothiocyanatopiperidine 2.NaBH4 or LiAlH4 reduction of 4-(2-benzothienyl)-4-hydroxycyclohexanone 18 and 4-(2-benzothienyl)-4-(piperidino)cyclohexanone oxime 35 gives the corresponding cis-diol 21 and cis-cyclohexane-1,4-diamine 36 as the major isomers which have been investigated as precursors to the cyclohexane ring isothiocyanates 3 and 4.Alternative routes to 3 and 4 are compared and their stereochemical outcome investigated.
