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| Formula | C17H23Cl2NO |
| Molar mass | 328.28 g·mol−1 |
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Cilobamine is a drug which acts as anorepinephrine-dopamine reuptake inhibitor (NDRI) and hasstimulant andantidepressant effects.[1][2]
It can clearly be seen that the structure is based ondichloroisoprenaline that has been fused onto the bicycloalkane scaffold.
An intramolecularDieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate (3) withsodium hydride base provides methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate (4). Treatment withsodium nitrite introduces anisonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo[2.2.2]octan-2-one (5). Addition of the arylGrignard reagent, and reduction of theoxime gives (6). Areductive amination of the primary amino group with acetone then completes the synthesis of cilobamine (7).
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| D1-like |
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| D2-like |
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