2,6-Dimethylpiperidine

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2,6-Dimethylpiperidine
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colorless liquid
Density 0.84 g/mL
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Solubility in other solvents Most organic solvents
Basicity (pKb) ca. 10
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Template:Longitem Piperidine

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2,6-Dimethylpiperidines are chemical compounds with the formula C5H8(CH3)2NH. Three stereoisomers exist: the achiral (R,S)-isomer and the chiral (R,R)/(S,S) enantiomeric pair. Dimethylpiperidines are derivatives of the heterocycle piperidine, wherein two hydrogen atoms are replaced by methyl groups.

The 2,6-dimethylpiperidines are prepared by reduction of 2,6-dimethylpyridine (2,6-lutidine). The achiral isomer is the predominant isomer produced in this reaction.

The 2,6-dimethylpiperidines are of interest for their conformational properties. The (R,S)-isomer exists largely in the chair conformation with equatorial methyl groups. The (R,R)/(S,S)-isomers are attractive chiral secondary amine building blocks.[1]

References

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  1. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbuch, M.-T. and Pierre, J.-L., "Synthesis and resolution of a chiral analog of 2,2,6,6-tetramethylpiperidine and of its corresponding nitroxide", Tetrahedron Letters, 1998, volume 39, pages 2565-2568

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See also

Compound Summary 2,6-Dimethylpiperidine on National Library of Medicine National Center