Journal of the Chemical Society. Perkin transactions I p. 1671 - 1680 (1992)
Update date:2022-08-04
Topics:
Costa, Brian de
George, Clifford
Dominguez, Celia
Isomeric isothiocyanate derivatives 2-7 of the potent dopamine re-uptake (DA) inhibitor 1-<1-(2-benzothienyl)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.
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