4- (1-pyrrolidinyl) -piperidine - 4-(1-pirrolidinil)-piperidina
|4- (1-pyrrolidinyl) -piperidine|
|Semi-developed formula||CH 2 (CH 2 ) 3 N -CH 2 (CH 2 ) 4 NH|
|Density||1000 kg/m³; 1 g/cm³|
|Molar mass||154.25 g / mol|
|Melting point||56 °C (329 K)|
|Boiling point||230 °C (503 K)|
|Vapor pressure||0,1 ± 0,5 mmHg|
|Refractive index (n D )||1,508|
|Solubility in water||71 g/L|
|Flash point||365,15 K (92 °C)|
|heterocyclic amines|| Pyrrolidine |
|pyrrolidine-piperidine||3- (1-pyrrolidinyl) -piperidine|
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
The 4- (1-pyrrolidinyl) -piperidine is an organic compound of molecular formula C 9 H 18 N 2 . Its chemical structure contains a pyrrolidine ring and a piperidine ring ; it is a diamine with a tertiary amino group - on the pyrrolidine ring - and a secondary one - on the piperidine ring.
Physical and chemical characteristics
At room temperature, 4- (1-pyrrolidinyl) -piperidine is a solid that can occur as a white powder or crystals. [ 2 ] It has its melting point at 56 ºC —experimental value—, while its boiling point is at 230 ºC —theoretical value. Similarly density than water (ρ = 1.0 g / cm³), is little soluble in it, in ratio of about 71 g / L . The value of the logarithm of its partition coefficient , log P = 0.96, shows that its solubility is higher in nonpolar solvents such as 1-octanolthan in water. [ 3 ] [ 4 ]
Synthesis and uses
This diamine has been used for the synthesis of bromides with pyrrolidine and piperidine rings. Likewise, it forms Hoffmann-type complexes , having studied the complexes [M (4- pypp ) 2 Ni (CN) 4 ], where M = Ni or Co, and pypp are the acronym for 4- (1-pyrrolidinyl) -piperidine . [ 7 ]
In biology, 4- (1-pyrrolidinyl) -piperidine has been used as a reagent in the synthesis of small ligands for proteins linked to methyl-lysine , said proteins being important components of epigenetic regulation ; also to make molecules that restore E-cadherin , which limits the proliferation of colorectal carcinoma cells . Another biological use of this amine is in the synthesis of IKKβ inhibitors, [ 7 ] compounds related to a small group of transcription factors ( proteinscalled NF-κB) that play an important role in the regulation of inflammatory, immune and apoptotic responses . [ 8 ] On the other hand, new analogues of 4- (1-pyrrolidinyl) -piperidine capable of regulating glucose level in blood plasma have been synthesized and investigated . [ 9 ]
4- (1-Pyrrolidinyl) -piperidine is a corrosive and irritating substance. Its contact can cause severe burns to the skin and eyes. [ 5 ]
The following compounds are isomers of 4- (1-pyrrolidinyl) -piperidine:
- 1- (2-pyrrolidinylmethyl) pyrrolidine
- CAS number
- 4-(1-Pyrrolidinyl)piperidine(5004-07-9) (Chemical Book)
- 4-(1-Pyrrolidinyl)piperidine (PubChem)
- 4-(1-Pyrrolidinyl)piperidine (ChemSpider)
- 4-(1-Pyrrolidinyl)piperidine. Safety Sheet. (Alfa Aesar)
- 4-(1-Pyrrolidinyl)piperidine 5004-07-9 Synthesis Route (Molbase)
- 4-(1-Pyrrolidinyl)piperidine (Sigma-Aldrich)
- Chung-Hang Leung, Daniel Shiu-Hin Chan, Ying-Wei Li, Wang-Fun Fong, Dik-Lung Ma (2013). «Hit identification of IKKβ natural product inhibitor». BMC Pharmacology and Toxicology 14 (3). Consultado el 23 de junio de 2016.
- Mushtaq N, Saify ZS, Akhtar S, Arif M, Haider S, Saba N. (2010). «Synthesis of some novel analogues of 4-(1-Pyrrolidinyl) Piperidine and their effect on plasma glucose level». Pak J Pharm Sci. 23 (2): 220-223. Consultado el 23 de junio de 2016.