Synthesis of [9,10-Dihydro-9-(2-methylaminoethyl)-9,10propanoanthracene]

Reaction of anthrone R1 with Grignard reagent to give 9-substituted anthracene R2 which treatment with αbromoacroline to give R3. Reaction of R3 with 1M NaOH resulted in transformation into the ring expanded α-hydroxy ketone R4. Transformation of α-hydroxy ketone by using samarium diiodide led to the desired key intermediate ketone R5, which treatment with hydrazine hydrate to afford tetracyclic hydrocarbon R6, which Reaction with BH3 to give alcohol R7. Conversion alcohol into the chloride by using triphenylphosphane in CCl4 to gave R8. Interaction of R8 with methyl amine in methanol afforded Bishomobenzoctamine R9, Scheme 1 as a homologue of the anxiety benzoctamine R.