''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 Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...

Preparation

''N''-Hydroxypiperidine can be prepared from the application of ''meta''-chloroperoxybenzoic acid and methanol to the tertiary amine product of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...

and

, followed by heating with acetone of the resulting tertiary ''N''-oxide.

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.

References

{{DEFAULTSORT:Hydroxypiperdine, N- 1-Piperidinyl compounds Hydroxylamines