4- (1-pyrrolidinyl) pyridine

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Structural formula
Structure of PPY
General
Surname 4- (1-pyrrolidinyl) pyridine
other names
  • PPY
  • 4-pyrrolidine pyridine
Molecular formula C 9 H 12 N 2
Brief description

yellow solid

External identifiers / databases
CAS number 2456-81-7
EC number 219-534-2
ECHA InfoCard 100,017,759
PubChem 75567
ChemSpider 68092
Wikidata Q229878
properties
Molar mass 148.20 g mol −1
Physical state

firmly

Melting point

54-58 ° C

boiling point

171–173 ° C (27 h Pa )

solubility
  • bad in water at 20 ° C
  • moderately in methanol
safety instructions
GHS labeling of hazardous substances
05 - Corrosive 06 - Toxic or very toxic

danger

H and P phrases H: 301-314
P: 280-301 + 310-305 + 351 + 338-310
Toxicological data

176 mg kg −1 ( LD 50 ,  rat ,  oral )

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 . It is used in acylations to activate the carboxylic acid anhydrides , inducing significantly higher reaction kinetics than pyridine. Even faster reaction rates are achieved than with 4-DMAP .

presentation

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

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, RE 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 .