Chemistry:Diacetonamine
Diacetonamine is a useful precursor in organic synthesis.
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 aplication 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]
References
- ↑ "Formation of diacetonamine and triacetonamine in plant extracts". Phytochemistry 6 (11): 1587–1588. November 1967. doi:10.1016/S0031-9422(00)82956-8. Bibcode: 1967PChem...6.1587S.
- ↑ 2.0 2.1 The organic chemistry of drug synthesis. 1. Wiley. 1977. ISBN 9780471521419.
- ↑ "Compounds Affecting the Central Nervous System. I. 4-Piperidones and Related Compounds". Journal of Medicinal Chemistry 8 (5): 619–625. September 1965. doi:10.1021/jm00329a015. PMID 5867943.
- ↑ Ganellin Charon Robin & Spickett Robert Geoffr William, U.S. Patent 3,067,204 (1962 to Smith Kline and French Laboratories Ltd).
- ↑ "240. Experiments in the piperidine series. Part II". Journal of the Chemical Society (Resumed): 917. 1945. doi:10.1039/jr9450000917.
- ↑ "CCCLXVIII.—Some derivatives of the vinyldiacetonalkamines". J. Chem. Soc., Trans. 123: 3115–3119. 1923. doi:10.1039/CT9232303115.
- ↑ Organic medical chemicals, by M. Barrowliff, 98, 1921.
- ↑ "Preparation of Diacetonamine.". Journal of the American Chemical Society 47 (4): 1195–1196. April 1925. doi:10.1021/ja01681a504. Bibcode: 1925JAChS..47.1195H.
- ↑ "XLVIII.—The preparation of diacetonamine". J. Chem. Soc., Trans. 115: 588–592. 1919. doi:10.1039/CT9191500588.
- ↑ 10.0 10.1 "Diacetonamine Hydrogen Oxalate". Organic Syntheses 6: 28. 1926. doi:10.15227/orgsyn.006.0028.
- ↑ 11.0 11.1 (Experiment 8 & 12) A Class-Book of Organic Chemistry, by J. B. Cohen, 12, 1919.
- ↑ "Ueber die Einwirkung des Ammoniaks auf Aceton". Berichte der Deutschen Chemischen Gesellschaft 7 (2): 1384–1387. July 1874. doi:10.1002/cber.187400702137.
- ↑ "ACTION OF LIQUID AMMONIA UPON ACETOONE COMPOUNDS OF α-HYDROXY-ACIDS". Bulletin of the Chemical Society of Japan 11 (6): 385–389. 1 June 1936. doi:10.1246/bcsj.11.385.
- ↑ "Rückverwandlung des Triacetonamins in Diacetonamin und eine fünfte Acetonbasis". Justus Liebigs Annalen der Chemie 181 (1): 70–89. January 1876. doi:10.1002/jlac.18761810107.
- ↑ "Synthesis of hexahydro-3,3,5,5,7-pentaalkyl-2H-1,4-diazepin-2-ones from 1,3-diamines and ketones". The Journal of Organic Chemistry 46 (2): 323–327. January 1981. doi:10.1021/jo00315a020.
- ↑ "MESITYL OXIDE". Organic Syntheses 1: 53. 1921. doi:10.15227/orgsyn.001.0053.
- ↑ "XXXIII.—The action of ammonia on acetone". J. Chem. Soc., Trans. 119: 269–271. 1921. doi:10.1039/CT9211900269.
- ↑ "261. The reaction between acetone and ammonia : the formation of pyrimidine compounds analogous to the aldoxans of späth". J. Chem. Soc. 0: 1394–1399. 1947. doi:10.1039/JR9470001394.
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