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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 [1401222-79-4] (3) with sodium hydride base gives reaction Methyl 3-oxobicyclo[2.2.2]octane-2-carboxylate [30144-30-0] (4). Treatment withsodium 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 givesCID:154108204 (6). A reductive amination of the primary amino group with acetone then completed the synthesis of cilobamine (7).
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| D1-like |
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| D2-like |
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