4-(1-Pyrrolidinyl)pyridin - 4-(1-Pyrrolidinyl)pyridin

Structural formula
Structure of PPY
General
Name 4-(1-Pyrrolidinyl)pyridin
other names
  • PPY
  • 4-Pyrrolidinpyridin
Sum formula C9H12N2
Brief description

yellow solid [1]

External identifiers / databases
CAS number 2456-81-7
EC number 219-534-2
ECHA-InfoCard 100.017.759
PubChem 75567
ChemSpider 68092
Wikidata Q229878
characteristics
Molar mass 148.20 g · mol −1
Physical state

fest

Melting point

54–58 °C[1]

boiling point

171–173 °C (27 hPa)[1]

solubility
safety instructions
GHS hazard labeling [2]
05 - Corrosive 06 - Toxic or very toxic

danger

H and P phrases H: 301​‐​314
P: 280​‐​301+310​‐​305+351+338​‐​310 [2]
Toxicological data

176 mg·kg−1 (LD50, Ratte, oral)[1]

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4- (1-Pyrrolidinyl) pyridine is an organic compound from the field of heterocycles . Is a pyridine ring , the in-4 position with a 1-linked pyrrolidine substituted is. PPY was discovered in 1969 by Wolfgang Steglich . [3] It is used in acylations to activate the carboxylic acid anhydrides , whereby it induces significantly higher reaction kinetics than pyridine. Even faster reaction rates are achieved than with 4-DMAP . [4]

presentation

PPY can be obtained in good yield by reaction of pyridine with thionyl chloride and subsequent reaction with N -formylpyrrolidine . [4] The reaction of 4-chloropyridine with pyrrolidine by microwave irradiation also gives PPY in very good yield. [5]

Individual evidence

  1. a b c d e Data sheet 4- (1-pyrrolidinyl) pyridine (PDF) from Merck , accessed on June 27, 2010.
  2. a b c data sheet 4-pyrrolidinopyridine from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
  3. W. Steglich, G. Höfle: 4-Dimethylaminopyridine, a highly effective acylation catalyst , in: Angew. Chem. 1969 , 81 , 1001; doi: 10.1002 / anie.19690812313 .
  4. a b G. Höfle, W. Steglich, H. Vorbrüggen: 4-Dialkylaminopyridines as highly effective acylation catalysts , in: Angew. Chem. 1978 , 90 , 602-615; doi: 10.1002 / anie.19780900806 .
  5. S. Narayan, T. Seelhammer, R. E. Gawley: Microwave assisted solvent free amination of halo-(pyridine or pyrimidine) without transition metal catalyst, in: Tetrahedron Lett. 2004, 45, 757–759; doi:10.1016/j.tetlet.2003.11.030.