Diacetonamine
Chemical compound
From Wikipedia, the free encyclopedia
Diacetonamine is a useful precursor in organic synthesis.
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| Names | |
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| Other names
4-Amino-4-methylpentan-2-one | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.009.888 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H13NO | |
| Molar mass | 115.17 g/mol |
| Density | g/cm3 (20°C) |
| Boiling point | 163 °C (325 °F; 436 K) at 12 mm Hg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diacetonamine and triacetonamine are formed in plant extracts:[1]
Diacetonamine contains an acetyl group, a primary amine, and two methyl groups.
Applications
It is known to have application in the synthesis of eucaine[2] & alpha-eucaine.[2]
-2,2-dimethylpiperidin-4-one.svg)
Additionally it was used in the synthesis of [2104-81-6], an agent discovered by C. Robin Ganellin.[3][4] 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.[5]
Another place that diacetonamine is used is in the synthesis of Eucatropine (euphtalmin) [100-91-4].[6] The synthesis route is via the precursor 2,2,6-trimethylpiperidin-4-one [3311-23-7].[7] This is the same chemical as was used in the synthesis of beta-eucaine (see above).
Synthesis
It is formed by the conjugate addition of ammonia to mesityl oxide.[8][9][10][11][12][13][14][15] Mesityl oxide itself is formed from the dehydration of diacetone alcohol.[16] 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.[11][10] However, closer inspection of the literature reveals that different products are obtained from this reaction.[17][18]