The syntheses of radiolabelled org 5222 and its main metabolite org 30526

✍ Scribed by Jan Vader; Frans Kaspersen; Eric Sperling; Irene Schlachter; Annie Terpstra; Peter Hilberink; Gerard Wagenaars

• Book ID: 102901503
• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: French
• Weight: 883 KB
• Volume: 34
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580340907

✦ Synopsis

Abstract

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