Diacetonamine

Diacetonamine
Names
Other names
4-Amino-4-methylpentan-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.888
EC Number
  • 210-876-8
UNII
  • InChI=1S/C6H13NO/c1-5(8)4-6(2,3)7/h4,7H2,1-3H3
    Key: CQTRUFMMCCOKTA-UHFFFAOYSA-N
  • CC(=O)CC(C)(C)N
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).
Infobox references

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 application in the synthesis of eucaine[2] & alpha-eucaine.[2]

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

  1. ^ Stewart, I., Wheaton, T. A. (November 1967). "Formation of diacetonamine and triacetonamine in plant extracts". Phytochemistry. 6 (11): 1587–1588. Bibcode:1967PChem...6.1587S. doi:10.1016/S0031-9422(00)82956-8.
  2. ^ a b Lednicer, D., Mitscher, L. A. (1977). The organic chemistry of drug synthesis. 1. Wiley. ISBN 9780471521419.
  3. ^ Ganellin, C. R., Spickett, R. G. W. (September 1965). "Compounds Affecting the Central Nervous System. I. 4-Piperidones and Related Compounds". Journal of Medicinal Chemistry. 8 (5): 619–625. doi:10.1021/jm00329a015. PMID 5867943.
  4. ^ Ganellin Charon Robin & Spickett Robert Geoffr William, U.S. patent 3,067,204 (1962 to Smith Kline and French Laboratories Ltd).
  5. ^ Anker, R. M., Cook, A. H., Heilbron, I. M. (1945). "240. Experiments in the piperidine series. Part II". Journal of the Chemical Society (Resumed): 917. doi:10.1039/jr9450000917.
  6. ^ Kipping, F. S. (1923). "CCCLXVIII.—Some derivatives of the vinyldiacetonalkamines". J. Chem. Soc., Trans. 123: 3115–3119. doi:10.1039/CT9232303115.
  7. ^ Organic medical chemicals, by M. Barrowliff, 98, 1921.
  8. ^ Haeseler, P. R. (April 1925). "Preparation of Diacetonamine". Journal of the American Chemical Society. 47 (4): 1195–1196. Bibcode:1925JAChS..47.1195H. doi:10.1021/ja01681a504.
  9. ^ Everest, A. E. (1919). "XLVIII.—The preparation of diacetonamine". J. Chem. Soc., Trans. 115: 588–592. doi:10.1039/CT9191500588.
  10. ^ a b "Diacetonamine Hydrogen Oxalate". Organic Syntheses. 6: 28. 1926. doi:10.15227/orgsyn.006.0028.
  11. ^ a b (Experiment 8 & 12) A Class-Book of Organic Chemistry, by J. B. Cohen, 12, 1919.
  12. ^ Sokoloff, N., Latschinoff, P. (July 1874). "Ueber die Einwirkung des Ammoniaks auf Aceton". Berichte der Deutschen Chemischen Gesellschaft. 7 (2): 1384–1387. doi:10.1002/cber.187400702137.
  13. ^ Ôeda, H. (1 June 1936). "ACTION OF LIQUID AMMONIA UPON ACETOONE COMPOUNDS OF α-HYDROXY-ACIDS". Bulletin of the Chemical Society of Japan. 11 (6): 385–389. doi:10.1246/bcsj.11.385.
  14. ^ Heintz, W. (January 1876). "Rückverwandlung des Triacetonamins in Diacetonamin und eine fünfte Acetonbasis". Justus Liebigs Annalen der Chemie. 181 (1): 70–89. doi:10.1002/jlac.18761810107.
  15. ^ Son, P.-N., Lai, J. T. (January 1981). "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. doi:10.1021/jo00315a020.
  16. ^ "MESITYL OXIDE". Organic Syntheses. 1: 53. 1921. doi:10.15227/orgsyn.001.0053.
  17. ^ Patterson, T. S., McMillan, A. (1921). "XXXIII.—The action of ammonia on acetone". J. Chem. Soc., Trans. 119: 269–271. doi:10.1039/CT9211900269.
  18. ^ Bradbury, R. B., Hancox, N. C., Hatt, H. H. (1947). "261. The reaction between acetone and ammonia : the formation of pyrimidine compounds analogous to the aldoxans of späth". J. Chem. Soc. 0: 1394–1399. doi:10.1039/JR9470001394.
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