4-Amino-2,2,6,6-tetramethylpiperidine explained

4-Amino-2,2,6,6-tetramethyl-4-piperidine is an organic compound with the formula H₂NCH(CH₂CMe₂)₂NH (where Me = CH₃). Classified as a diamine, it is a colorless oily liquid.

The compound is an intermediate in the preparation of Bobbitt's salt, an oxidant used in organic synthesis. It is prepared by the reductive amination of the corresponding ketone:^[1]

OC(CH₂CMe₂)₂NH + NH₃ + H₂ → H₂NCH(CH₂CMe₂)₂NH + H₂O

Compound Properties

Boiling point is 188.5 °C ^[2] Melting point is 17 °C. ^[3] Density is 0.8966 g/cm3 @ Temp: 20 °C ^[4]

Toxicity

A study by Truda et al, has reported the median lethal dose LD(50) as 906mg/kg in rats. .^[5]

References

1. Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review. Nabyl Merbouh . James M. Bobbitt . Christian Brückner. 2004. Organic Preparations and Procedures International. 36. 1–31. 10.1080/00304940409355369. 98117103 .
2. PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4
3. PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4
4. PhysProp data were obtained from: https://commonchemistry.cas.org/detail?cas_rn=36768-62-4
5. Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(5), Pg. 53, 1984

Related compounds

• Pempidine
• 2,2,6,6-Tetramethylpiperidine

Further reading

• Rapid Microwave-Assisted Syntheses of Derivatives of HIV-1 Entry Inhibitors . C. McFarland . D. Vicic . A. Debnath . . 2006. 2006 . 807–812 . 10.1055/s-2006-926339 . 5.
• A Revised Preparation of (4-Acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate: Reagents for Stoichiometric Oxidations of Alcohols . L. Tilley . J. Bobbitt . S. Murray . C. Camire . Synthesis. 2013. 45 . 326–329 . 10.1055/s-0032-1317861. 3.
• Comparative characteristics of the toxicity, safety and nature of the biological effect on the body of 4-hydroxy-2,2,6,6-tetramethylpiperidine and 4-amino-2,2,6,6-tetramethylpiperidine. A. Germanova . L. Aizvert . A. Shidlovskaia . L. Melnikova . M. Bidevkina . . 1984. 53–54 . 6745687. 5.
• 4-Amino-TEMPO as N-Nucleophile in Palladium-Catalyzed Aminocarbonylation . M. Gergely . A. Takacs . L.Kollar . . 2016 . 54 . 634–640 . 10.1002/jhet.2635 . 1.