Diacetonamine
Diacetonamine is a useful precursor in organic synthesis.
Diacetonamine and triacetonamine are formed in plant extracts:
Diacetonamine contains an acetyl group, a primary amine, and two methyl groups.
Applications
It is known to have application in the synthesis of eucaine & alpha-eucaine.Additionally it was used in the synthesis of , an agent discovered by C. Robin Ganellin. This compound has central nervous system activity as a combination of a stimulant and a depressant. A narcotic pharmacophore was associated with the structure in an earlier work.
Another place that diacetonamine is used is in the synthesis of Eucatropine . The synthesis route is via the precursor 2,2,6-trimethylpiperidin-4-one . This is the same chemical as was used in the synthesis of beta-eucaine.
Synthesis
It is formed by the conjugate addition of ammonia to mesityl oxide. Mesityl oxide itself is formed from the dehydration of diacetone alcohol. However, it can also be prepared directly from acetone without isolating the intermediate alcohol.It is claimed that diacetonamine can also be prepared by the direct reaction between ammonia and acetone. However, closer inspection of the literature reveals that different products are obtained from this reaction.