N-Hydroxypiperidine

<i>N</i>-Hydroxypiperidine

N-Hydroxypiperidine

Chemical compound

N-Hydroxypiperidine (also known as 1-piperidinol and 1-hydroxypiperidine) is the chemical compound with formula C5H11NO. It is a hydroxylated derivative of the heterocyclic compound piperidine.

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Preparation

N-Hydroxypiperidine can be prepared from the application of meta-chloroperoxybenzoic acid and methanol to the tertiary amine product of acrylonitrile and piperidine, followed by heating with acetone of the resulting tertiary N-oxide.[1]

Reactions

N-Hydroxypiperidine is a secondary amine, which can undergo an oxidation reaction with hydrogen peroxide in methanol as the solvent. This produces a nitrone, which is heteroatomic equivalent to a ketone with a nitrogen instead of an alpha carbon. Competing elimination reactions can occur, as well.[2]

References

  1. [1]
    O’Neil, I. A.; Cleator, E.; Tapolczay, D. J. A convenient synthesis of secondary hydroxylamines. Tetrahedron Letters, 2001, 42, pp. 8247–8249
  2. [2]
    Zauche, Timothy H.; Espenson, James H. (1997). "Kinetics and Mechanism of the Oxidation of Secondary Hydroxylamines to Nitrones with Hydrogen Peroxide, Catalyzed by Methylrhenium Trioxide". Inorganic Chemistry. 36 (23): 5257. doi:10.1021/ic970649d.
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