Dolbier HW Solutions 554

Dolbier HW Solutions 554 - 648 AMINES Conversion of this...

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Conversion of this intermediate to the desired N -methyl-4-piperidone requires a Dieckmann cyclization followed by decarboxylation of the resulting b -keto ester. Treatment of N -methyl-4-piperidone with the Grignard reagent derived from bromobenzene gives a tertiary alcohol that can be dehydrated to an alkene. Hydrogenation of the alkene completes the synthesis. 22.44 Sodium cyanide reacts with alkyl bromides by the S N 2 mechanism. Reduction of the cyano group with lithium aluminum hydride yields a primary amine. This reveals the structure of mescaline to be 2-(3,4,5-trimethoxyphenyl)ethylamine. 22.45 Reductive amination of a ketone with methylamine yields a secondary amine. Methamphetamine is N -methyl-1-phenyl-2-propanamine. 22.46 There is no obvious reason why the dimethylamino group in 4-( N , N -dimethylamino)pyridine should 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.

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