1228556-60-2

Usage

Uses

Used in Pharmaceutical Research:
2-(4-Methoxyphenyl)piperidine is utilized as a compound in pharmaceutical research for its potential pharmacological properties. It is studied for its possible applications as an antipsychotic and analgesic agent, given its capacity to interact with the nervous system and alleviate pain.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-Methoxyphenyl)piperidine is used as a precursor or building block for the development of new drugs. Its structural features allow for the creation of various derivatives with different therapeutic potentials.
Used in Dopamine Receptor Antagonist Development:
2-(4-Methoxyphenyl)piperidine is employed as a dopamine receptor antagonist, which can be crucial in the treatment of conditions like schizophrenia and Parkinson's disease, where dopamine imbalances are implicated.
Used in Neurodegenerative Disorder Treatment:
2-(4-METHOXYPHENYL)PIPERIDINE is being evaluated for its potential as a treatment for neurodegenerative disorders, given its possible neuroprotective effects and ability to modulate neurotransmitter systems involved in such conditions.
Used in Antagonist of the N-Methyl-D-Aspartate (NMDA) Receptor:
2-(4-Methoxyphenyl)piperidine is also being investigated for its potential as an antagonist of the NMDA receptor, which plays a significant role in learning, memory, and synaptic plasticity. Modulating NMDA receptor activity could provide therapeutic benefits for a range of neurological and psychiatric disorders.
As research and development in these areas progress, 2-(4-Methoxyphenyl)piperidine may lead to the discovery of new therapeutic agents for various medical conditions, offering innovative solutions to unmet medical needs.

Upstream product

• 63359-20-6 2-(4-methoxyphenyl)-piperidine hydrochloride 
• 1402834-94-9 (R)-N-allyl-N-(4-methoxybenzyl)-1-(4-methoxyphenyl)but-3-en-1-amine 
• 1402834-92-7 (R)-1-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine 
• 3261-60-7 N-(4-methoxybenzylidene)-4-methoxybenzylamine 
• 91640-07-2 6-(4-methoxyphenyl)-2,3,4,5-tetrahydropyridine 

Downstream Products

• 1402834-93-8 (R)-N-trifluroacetyl-2-(4-methoxyphenyl)piperidine 

Relevant academic research and scientific papers

Synthetic modifications of bifunctional homoallylamines: Synthesis of 2-arylpiperidines, (R)-anatabine and (R)-anabasine

The chiral homoallylamines with orthogonal bifunctional handle, an amine, and a pendant allyl unit are available to be easily converted into N-heterocycles. The N-allylation and Ru-catalyzed ring-closing metathesis delivered the bioactive 2-arylpiperidines, Nicotiana tabacum alkaloids (R)-anatabine and (R)-anabasine in three steps. A formal synthesis of (R)-N-methylanatabine and (R)-N-methylanabasine is also completed.

Structure, activity and stereoselectivity of NADPH-dependent oxidoreductases catalysing the S-selective reduction of the imine substrate 2-methylpyrroline

Oxidoreductases from Streptomyces sp. GF3546 [3546-IRED], Bacillus cereus BAG3X2 (BcIRED) and Nocardiopsis halophila (NhIRED) each reduce prochiral 2-methylpyrroline (2MPN) to (S)-2-methylpyrrolidine with >95 % ee and also a number of other imine substrates with good selectivity. Structures of BcIRED and NhIRED have helped to identify conserved active site residues within this subgroup of imine reductases that have S selectivity towards 2MPN, including a tyrosine residue that has a possible role in catalysis and superimposes with an aspartate in related enzymes that display R selectivity towards the same substrate. Mutation of this tyrosine residue - Tyr169 - in 3546-IRED to Phe resulted in a mutant of negligible activity. The data together provide structural evidence for the location and significance of the Tyr residue in this group of imine reductases, and permit a comparison of the active sites of enzymes that reduce 2MPN with either R or S selectivity.

Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

A novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining (R)-6-hydroxy-d-nicotine oxidase (6-HDNO) with an (R)-IRED, a panel of racemic 2-substituted piperidines and pyrrolidines were deracemized to yield the (S)-amines in high yields and enantiomeric excess values. Other N-heterocycles were deracemized with monoamine oxidase (MAO-N) or 6-HDNO in combination with ammonia borane, which allowed comparison of the two enzyme deracemization approaches with that involving a chemical reducing agent.

Enantioselective synthesis of substituted piperidines by addition of aryl grignard reagents to pyridine N-oxides

The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combinatio

Enantioselective allylation of imines catalyzed by newly developed (-)-β-pinene-based π-allylpalladium catalyst: An efficient synthesis of (R)-α-propylpiperonylamine and (R)-pipecolic acid

A newly developed π-allylpalladium with a (-)-β-pinene framework and an isobutyl side chain catalyzed the enantioselective allylation of imines in good yields and enantioselectivities (20 examples, up to 98% ee). An efficient enantioselective synthesis of the (R)-α-propyl piperonylamine part of DMP 777, a human leukocyte elastase inhibitor and (R)-pipecolic acid have been achieved as a useful application of this methodology. The Royal Society of Chemistry 2012.

Applications of N′-alkylated derivatives of TsDPEN in the asymmetric transfer hydrogenation of C=O and C=N bonds

Arene/Ru(II) complexes of (R,R)-N-alkyl-TsDPEN ligands are effective in the asymmetric transfer hydrogenation of ketones and imines in formic acid/triethylamine solution. The complex derived from the N′-Bn derivative of TsDPEN reduces monocyclic imines in up to 60% ee, whilst the N′-Me derivative of TsDPEN forms a more active catalyst than the non-alkylated analogue and reduces ketones in up to 97% ee.