4209-64-7

Usage

Chemical structure

Piperidine derivative with a benzyl group attached to the nitrogen atom and methyl groups at the 2 and 6 positions of the piperidine ring.

Pharmaceutical research

Building block for the synthesis of various drugs and bioactive compounds.

Neuroprotective properties

Studied for its potential neuroprotective effects.

Antidepressant properties

Investigated for its potential antidepressant properties.

Local anesthetic

Explored for its potential use as a local anesthetic.

Coordination chemistry

Investigated as a ligand in coordination chemistry.

Fields of interest

Medicine, pharmacology, and chemical research.

Upstream product

• 13505-34-5 2,6-heptandione 
• 100-44-7 benzyl chloride 
• 504-03-0 2.6-dimethylpiperidine 
• 100-46-9 benzylamine 
• 98195-16-5 (2S,6S)-1-Benzyl-2,6-dimethyl-piperidine-2,6-dicarbonitrile 

Relevant academic research and scientific papers

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.

Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6- dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6- heptanedione with hydride reagents

The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride reagents afforded 2,5- dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastereoselectivity, as the cis/trans ratio was affected by the size of the ring formed and the steric and electronic properties of the nitrogen substituent. Increasing the bulkiness of the nitrogen substituent, the cis pyrrolidines and the trans-piperidines were obtained with enhanced selectivity.