The syntheses of radiolabelled Org 5222 and its main metabolites Org 30526

Article abstract of DOI:10.1002/jlcr.2580340907

The syntheses of trans-5-chloro-2,3,3a-12b-tetrahydro-2-methyl-1H-dibenz [2,3:6,7]oxepino[4,5-c]pyrrole (Org 5222), a potential antipsychotic compound, labelled with ³H, ¹⁴C and ³⁶C1 and trans-5-chloro-2,3,3a,12b-tetrahydro-1H-dibenz[2,3:6,7]-oxepino[4,5-c] pyrrole (Org 30526) labelled with ³H are described. ³H-labelled Org 5222 of low specific activity was prepared by a base catalyzed exchange with tritiated water of an amide precursor, ³H-labelled Org 5222 with a high specific activity by a catalytic reductive dehalogenation. ³H-labelled Org 30526 was prepared both by demethylation of ³H-Org 5222 and by catalytic reductive iodination of 11-iodo-Org 30526. ¹⁴C-labelled Org 5222 was synthesized in 6 steps using ¹⁴C-sarcosine as starting material. ³⁶C1-labelled Org 5222 was prepared by diazotation reaction in the presence of H³⁶C1.