Conversion of this intermediate to the desired N-methyl-4-piperidone requires a Dieckmanncyclization followed by decarboxylation of the resulting b-keto ester.Treatment ofN-methyl-4-piperidone with the Grignard reagent derived from bromobenzene givesa tertiary alcohol that can be dehydrated to an alkene. Hydrogenation of the alkene completes thesynthesis.22.44Sodium cyanide reacts with alkyl bromides by the SN2 mechanism. Reduction of the cyano groupwith lithium aluminum hydride yields a primary amine. This reveals the structure of mescaline to be2-(3,4,5-trimethoxyphenyl)ethylamine.22.45Reductive amination of a ketone with methylamine yields a secondary amine. Methamphetamine isN-methyl-1-phenyl-2-propanamine.22.46There is no obvious reason why the dimethylamino group in 4-(N,N-dimethylamino)pyridineshould be appreciably more basic than it is in
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.