7250-70-6

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Methylphenyl)piperidine is utilized as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows it to be a valuable building block for the creation of new drugs targeting a range of medical conditions.
Used in Drug Development:
In the field of drug development, N-(2-Methylphenyl)piperidine serves as a crucial component in the formulation of novel therapeutic agents. Its properties make it suitable for the design and synthesis of medications aimed at treating various diseases and disorders.
Used in Research and Development:
N-(2-Methylphenyl)piperidine is also used as a research compound for exploring its potential psychoactive effects. While the exact mechanism of action is not yet fully understood, ongoing studies aim to elucidate its role in this area, potentially leading to new applications in the treatment of neurological or psychiatric conditions.
Overall, N-(2-Methylphenyl)piperidine is a versatile compound with applications spanning across the pharmaceutical industry, drug development, and research, making it an important asset for scientists and researchers in their quest to discover and create new medications and therapies.

InChI:InChI=1/C12H17N/c1-11-7-3-4-8-12(11)13-9-5-2-6-10-13/h3-4,7-8H,2,5-6,9-10H2,1H3

Upstream product

• 111-30-8 Glutaraldehyde 
• 95-53-4 o-toluidine 
• 111-29-5 1 ,5-pentanediol 
• 5542-49-4 piperidin-1-yl benzoate 
• 7029-31-4 bis(2-methylphenyl)zinc 
• 110-89-4 piperidine 
• 615-37-2 ortho-methylphenyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 3991-61-5 1-methyl-2-phenoxybenzene 
• 2156-71-0 N-chloropiperidine 
• 108-88-3 toluene 
• 352-70-5 m-Fluorotoluene 
• 95-49-8 2-methylchlorobenzene 
• 932-31-0 ortho-tolylmagnesium bromide 

Downstream Products

• 60815-16-9 2-(o-formylphenyl)-1-phenylethanone 
• 1260154-54-8 C₁₉H₁₉NO₂ 

Relevant academic research and scientific papers

Synthesis of N-heterocyclic carbene-Pd(II)-5-phenyloxazole complexes and initial studies of their catalytic activity toward the Buchwald-Hartwig amination of aryl chlorides

Three new N-heterocyclic carbene (NHC)-Pd(II) complexes using 5-phenyloxazole as the ancillary ligand have been obtained in moderate to good yields by a one-pot reaction of the corresponding imidazolium salts, palladium chloride and 5-phenyloxazole under mild conditions. Initial studies showed that one of the complexes is an efficient catalyst for the Buchwald-Hartwig amination of aryl chlorides with various secondary and primary amines under the varied catalyst loading of 0.01-0.05 mol%, thus it will enrich the chemistry of NHCs and give an alternative catalyst for the coupling of challenging while cost-low aryl chlorides.

Leaving Group Ability in Nucleophilic Aromatic Amination by Sodium Hydride-Lithium Iodide Composite

The methoxy group is generally considered as a poor leaving group for nucleophilic substitution reactions. This work verified the superior ability of the methoxy group in nucleophilic amination of arenes mediated by the sodium hydride and lithium iodide through experimental and computational approaches.

Electron Donor-Acceptor Complex-Initiated Photochemical Cyanation for the Preparation of α-Amino Nitriles

An electron donor-acceptor complex-initiated α-cyanation of tertiary amines has been described. The reaction protocol provides a novel method to synthesize various α-amino nitriles under mild conditions. The reaction can proceed smoothly without the presence of photocatalysts and transition metal catalysts, and either oxidants are unnecessary or O2 is the only oxidant. The practicality of this method is showcased not only by the late-stage functionalization of natural alkaloid derivatives and pharmaceutical intermediate, but also by the applicability of a stop-flow microtubing reactor.

Practical and regioselective amination of arenes using alkyl amines

The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.

N-Heterocyclic carbene-palladacyclic complexes: synthesis, characterization and their applications in the C-N coupling and α-arylation of ketones using aryl chlorides

N-Heterocyclic carbene-palladacyclic complexes 3 were successfully achieved in a one-pot procedure under mild conditions. The structure of 3a was unambiguously confirmed by X-ray single crystal diffraction and it was an active catalyst in the Buchwald-Hartwig amination and α-arylation of ketones even at very low catalyst loadings (0.01 mol%).

N-heterocyclic carbene-palladium complex, and preparation method and application thereof

The invention discloses an N-heterocyclic carbene-palladium complex, and a preparation method and application thereof. The N-heterocyclic carbene-palladium complex disclosed by the invention is shown in Formula (I), wherein L1 is a quinoline ligand or isoquinoline ligand, and N in the L1 is connected with Pd; L2 is an N-heterocyclic carbene ligand, and carbene carbon in the L2 is connected with the Pd; and X1 and X2 are respectively independently an anionic ligand. The N-heterocyclic carbene-palladium complex disclosed by the invention can efficiently catalyze carbon-carbon or carbon-heteroatom coupling reaction using aryl halide as a substrate. The formula is shown in the specification.

n-Butyllithium-mediated synthesis of N-aryl tertiary amines by reactions of fluoroarenes with secondary amines at room temperature

A simple and facile method for the synthesis of aromatic tertiary amines by amination of fluoroarenes with secondary amines in the presence of n-butyllithium at room temperature was reported.

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Synthesis and characterization of N-heterocyclic carbene-palladium(II) chlorides-1-methylindazole and -1-methylpyrazole complexes and their catalytic activity toward C-N coupling of aryl chlorides

A series of N-heterocyclic carbene-palladium(ii) chlorides-1-methylindazole and -1-methylpyrazole complexes was successfully synthesized and fully characterized by X-ray single crystal diffraction. In addition, initial investigations of their catalytic activity showed that they were efficient catalysts in the C-N coupling of primary and secondary amines with aryl chlorides at low catalyst loadings.

Synthesis of N-heterocyclic carbene-PdCl2-(iso)quinoline complexes and their application in arylamination at low catalyst loadings

A new type of N-heterocyclic carbene-PdCl2-(iso)quinoline complexes 3 were successfully achieved in acceptable to good yields from easily available starting materials under mild conditions, and their structures were unambiguously confirmed using X-ray single crystal diffraction. Furthermore, their catalytic activity toward Buchwald-Hartwig arylamination of aryl chlorides with primary and secondary amines was fully tested. Under the optimal reaction conditions, the expected arylated amines can be obtained in high to excellent yields at low catalyst loadings (0.005-0.05 mol%). It may be worth noting here that comparison of these complexes with other well-defined and easily available NHC-Pd(ii) complexes bearing different N-containing ancillary ligands was also carried out, showing their superior catalytic activity over all others.