N-Hydroxypiperidine

N-Hydroxypiperidine
Names
	Preferred IUPAC name Piperidin-1-ol
	Other names 1-Hydroxypiperidine
Identifiers
CAS Number	4801-58-5;
3D model (JSmol)	Interactive image;
Beilstein Reference	102726
ChemSpider	19696;
ECHA InfoCard	100.023.057
PubChem CID	24880003;
UNII	9ANQ5DB3A2 ;
CompTox Dashboard (EPA)	DTXSID9063611 ;
	InChI InChI=1S/C5H11NO/c7-6-4-2-1-3-5-6/h7H,1-5H2;
	SMILES ON1CCCCC1;
Properties
Chemical formula	C5H11NO
Molar mass	101.149 g·mol−1
Appearance	Fine white crystals
Density	1.070 g/cm3
Melting point	39.3 °C (102.7 °F; 312.4 K)
Boiling point	98.5 °C (209.3 °F; 371.6 K)
Solubility in water	113 g/L
log P	-0.17
Vapor pressure	0.542 Torr
Hazards
NFPA 704 (fire diamond)	0 2 0
Flash point	84.9 °C (184.8 °F; 358.0 K)
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

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

^ O’Neil, I. A.; Cleator, E.; Tapolczay, D. J. A convenient synthesis of secondary hydroxylamines. Tetrahedron Letters, 2001, 42, pp. 8247–8249
^ 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.

[1] O’Neil, I. A.; Cleator, E.; Tapolczay, D. J. A convenient synthesis of secondary hydroxylamines. Tetrahedron Letters, 2001, 42, pp. 8247–8249

[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.

[1]

[2]