Cilobamine
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Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.[1][2]
It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.
Synthesis
An intramolecular Dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate [1401222-79-4] (3) with sodium hydride base gives reaction Methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate [30144-30-0] (4). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one, CID:131066320 (5). Addition of the aryl Grignard reagent, and reduction of the oxime gives CID:154108204 (6). A reductive amination of the primary amino group with acetone then completed the synthesis of cilobamine (7).
See also
References
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- ↑ DE2003744 idem Jules Freedman, U.S. patent 3651142 (1970 to Colgate Palmolive Co).
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