Piperidine
Title: Piperidine
CAS Registry Number: 110-89-4
Additional Names: Hexahydropyridine
Molecular Formula: C5H11N
Molecular Weight: 85.15
Percent Composition: C 70.53%, H 13.02%, N 16.45%
Literature References: Found in small quantities in Piper nigrum L., Piperaceae (black pepper). May be obtained from piperine by heating with alcoholic KOH, or from 1,5-diaminopentane hydrochloride by cyclization. Usually prepd by electrolytic reduction of pyridine. Forms complexes with salts of heavy metals. Because of its reactivity, piperidine is useful in the prepn of cryst derivatives of aromatic nitro compds contg nuclear halogen atoms: Seikel, J. Am. Chem. Soc. 62, 750 (1940). Toxicity study: H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 23, 95 (1962). Review of physical constants of piperidine and N-alkyl piperidines: Magnusson, Schierz, Univ. Wyo. Publ. 7, 1 (1940).
Properties: Liquid. Characteristic odor. Soapy feel. Solidifies -13° to -17°; mp -7°; bp760 106°; bp20 18°; d420 0.8622; nD20 1.4534. Infrared absorption spectrum: Freymann, Compt. Rend. 205, 852 (1937); Ann. Chim. 11, 11 (1939). Ultraviolet and Raman spectra: Lecomte, Compt. Rend. 207, 395 (1938). Strong base: pK (25°): 2.80. Misc with water. Sol in alcohol, benzene, chloroform. LD50 orally in rats: 0.52 ml/kg (Smyth).
Melting point: mp -7°
Boiling point: bp760 106°; bp20 18°
pKa: pK (25°): 2.80
Index of refraction: nD20 1.4534
Density: d420 0.8622
Toxicity data: LD50 orally in rats: 0.52 ml/kg (Smyth)
 
Derivative Type: Hydrochloride
Molecular Formula: C5H11N.HCl
Molecular Weight: 121.61
Percent Composition: C 49.38%, H 9.95%, N 11.52%, Cl 29.15%
Properties: Orthorhombic prisms from alcohol, mp 247°. Freely sol in water, alcohol.
Melting point: mp 247°
 
Derivative Type: Nitrate
Molecular Formula: C5H11N.HNO3
Molecular Weight: 148.16
Percent Composition: C 40.53%, H 8.16%, N 18.91%, O 32.40%
Properties: Hygroscopic plates, sublimes 75° (10 mm), mp 110°. Freely sol in water, alcohol, ether. Absorption spectrum: Harper, Macbech, J. Chem. Soc. 107, 91 (1915).
Melting point: mp 110°
 
Derivative Type: Bitartrate
Molecular Formula: C5H11N.C4H6O6
Molecular Weight: 235.23
Percent Composition: C 45.95%, H 7.28%, N 5.95%, O 40.81%
Properties: Crystals, freely sol in water.
 
Derivative Type: Aurichloride
Molecular Formula: C5H11N.HAuCl4
Molecular Weight: 424.93
Percent Composition: C 14.13%, H 2.85%, N 3.30%, Au 46.35%, Cl 33.37%
Properties: Yellow crystals, mp 219°.
Melting point: mp 219°
 
Derivative Type: Platinichloride
Molecular Formula: 2C5H11N.H2PtCl6
Molecular Weight: 580.11
Percent Composition: C 20.70%, H 4.17%, N 4.83%, Pt 33.63%, Cl 36.67%
Properties: Yellow monoclinic prisms from water, mp 202°. Freely sol in water, slightly in alcohol.
Melting point: mp 202°
 
Derivative Type: N-Benzoylpiperidine
Properties: Long needles, mp 44-48°. Ref: Org. Synth. coll. vol. I (2nd ed., 1941) p 99.
Melting point: mp 44-48°
 
Derivative Type: Phosphate
CAS Registry Number: 767-21-5
Literature References: Prepn from piperidine + phosphoric acid: Abood, US 3035977 (1962).
Properties: Crystals, mp 204-206°.
Melting point: mp 204-206°

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