37035-03-3

Basic information

• Product Name: N-Phenyl-2,5-dimethylpyrrolidine
• Synonyms: N-Phenyl-2,5-dimethylpyrrolidine
• CAS NO: 37035-03-3
• Molecular Weight: 175.274
• Mol File: 37035-03-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-Phenyl-2,5-dimethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-2,5-dimethylpyrrolidine(37035-03-3)
• EPA Substance Registry System: N-Phenyl-2,5-dimethylpyrrolidine(37035-03-3)

Safety Data

• Hazardous Substances Data: 37035-03-3(Hazardous Substances Data)

Upstream product

• 1333-74-0 hydrogen 
• 110-13-4 2,5-hexanedione 
• 98-95-3 nitrobenzene 
• 592-45-0 1,4-hexadiene 
• 62-53-3 aniline 
• 592-42-7 1,5-Hexadien 
• 3031-66-1 3-hexyn-2,5-diol 
• 1003-38-9 2,5-dimethyltetrahydrofuran 
• 2935-44-6 hexane-2,5-diol 

Downstream Products

• 83-24-9 2,5-dimethyl-1-phenyl-1H-pyrrole 

Relevant articles and documents

gem-cyclodialkylation A facile synthetic route to N-substituted heterocycles

N-alkylated and N-arylated pyrroles, pyrrolidines, and piperidines are synthesized in high yield by the reaction between cyclic ethers and primary amines over a heterogeneous titania catalyst.

DIASTEREOSELECTIVE ELECTROCHEMICAL REDUCTIVE AMINATION OF 2,5-HEXANEDIONE AND 2,6-HEPTANEDIONE

The electrochemical reductive amination of 2,5-hexanedione with ammonia and 1-phenylethylamine at the mercury cathode afforded the corresponding 2,5-dimethylpyrrolidines with satisfactory yield and excellent cis-selectivity (90-98percent), but with arylamines mixtures of pyrroles and diastereoisomeric pyrrolidines were obtained.Only pyrroles were obtained with methyl- and benzylamine.On the other hand, 2,6-dimethylpiperidine (98percent cis) was obtained in low yield from 2,6-heptanedione and ammonia.The stereochemical outcome, along with the observation of a single reduction peak for the overall four-electron reduction, is consistent with a mechanism involving reduction of iminium ions, where the diastereoselctivity is controlled in the protonation of cyclic α-aminoalkyl radicals at the radical carbon atom.However, an alternative mechanism, involving the reduction of radicals to the corresponding carbanions followed by fast protonation, although less probable, could not be discarded.

One-Pot Synthesis of Substituted Pyrrolidines via Aminomercuration-Demercuration of 1,4- and 1,5-Hexadiene

The aminomercuratione-demercuration of 1,4- and 1,5-hexadiene yield cis- and trans-2,5-dimethyl-N-arylpyrrolidines via one-pot process.The intermolecular cyclization reaction goes through the corresponding mercurated pyrrolidines; these intermediates were isolated and characterized when the mercuration reaction was completed.The high stereoselectivity observed allows an easy way of synthesis for N-substituted trans-2,5-dimethylpyrrolidines.