4- (1-pyrrolidinyl) -piperidine - 4-(1-pirrolidinil)-piperidina

4- (1-pyrrolidinyl) -piperidine
4- (1-pyrrolidinyl) -piperidine.tif
4- (1-pyrrolidinyl) -piperidine-3D.gif
IUPAC name
As 4-pyrrolidin-1-ylpiperidine
General
Other names 4-pyrrolidinopiperidine
4-pyrrolidinylpiperidine
Semi-developed formula CH 2 (CH 2 ) 3 N -CH 2 (CH 2 ) 4 NH
Molecular formula C9H18N2
Identifiers
CAS number 5004-07-9[1]
ChemSpider 71049
PubChem 78703
Physical properties
Appearance Solid white
Density 1000 kg/; 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
Chemical properties
Solubility in water 71 g/L
log P 0,96
Family Amina
Dangerousness
Flash point 365,15 K (92 °C)
Related compounds
heterocyclic amines Pyrrolidine
Piperidine
Nanofina
Azepano
Azocano
Azecano
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 ]

This substance is incompatible with strong oxidizing agents and with carbon dioxide . [ 5 ]

Synthesis and uses

4- (1-pyrrolidinyl) -piperidine can be synthesized from 1-boc-4-piperidone or also from N -benzyl-4-piperidone. [ 6 ]

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 ]

Precautions

4- (1-Pyrrolidinyl) -piperidine is a corrosive and irritating substance. Its contact can cause severe burns to the skin and eyes. [ 5 ]

See also

The following compounds are isomers of 4- (1-pyrrolidinyl) -piperidine:

References

  1. CAS number
  2. 4-(1-Pyrrolidinyl)piperidine(5004-07-9) (Chemical Book)
  3. 4-(1-Pyrrolidinyl)piperidine (PubChem)
  4. 4-(1-Pyrrolidinyl)piperidine (ChemSpider)
  5. a b 4-(1-Pyrrolidinyl)piperidine. Safety Sheet. (Alfa Aesar)
  6. 4-(1-Pyrrolidinyl)piperidine 5004-07-9 Synthesis Route (Molbase)
  7. a b 4-(1-Pyrrolidinyl)piperidine (Sigma-Aldrich)
  8. 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.
  9. 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.