16819-50-4

Upstream product

• 100-44-7 benzyl chloride 
• 87-62-7 2,6-dimethylaniline 
• 18109-39-2 N-(2,6-diimethylphenyl)benzamide 
• 100-51-6 benzyl alcohol 
• 81889-77-2 benzyl(2,6-dimethylphenyl)carbamic chloride 
• 81-20-9 2,6-dimethylnitrobenzene 
• 108-88-3 toluene 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 617-86-7 triethylsilane 
• 3096-95-5 2,6-dimethyl-N-(benzylidene)aniline 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 100-46-9 benzylamine 
• 576-22-7 2-Bromo-m-xylene 

Downstream Products

• 125486-26-2 N-benzyl-2-chloro-N-(2,6-dimethyl-phenyl)-acetamide 
• 81889-77-2 benzyl(2,6-dimethylphenyl)carbamic chloride 
• 404826-05-7 N⁴,N^4'-dibenzyl-3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diamine 
• 1438900-66-3 N⁴,N⁴,N^4',N^4'-tetrabenzyl-3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diamine 
• 830326-43-7 (S)-2-(Benzhydrylidene-amino)-6-chloro-hexanoic acid benzyl-(2,6-dimethyl-phenyl)-amide 
• 830326-45-9 (S)-1-Benzhydryl-piperidine-2-carboxylic acid benzyl-(2,6-dimethyl-phenyl)-amide 
• 830326-42-6 2-(benzhydrylidene-amino)-N-benzyl-N-(2,6-dimethyl-phenyl)-acetamide 
• 830326-44-8 2-azido-N-benzyl-N-(2,6-dimethyl-phenyl)-acetamide 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 
• 27262-47-1 levobupivacaine 
• 35517-67-0 N-Benzyl-N-(2,6-dimethyl-phenyl)-formamide 
• 97018-24-1 4-[N-benzyl-N-(2,6-dimethyl-phenyl)-glycyl]-morpholine 
• 13405-92-0 N-benzyl-2,6-dimethyl-N-nitroso-aniline 

Relevant academic research and scientific papers

Reduction of imines with a reusable bimetallic PdCo-Fe3O4catalyst at room temperature under atmospheric pressure of H2

Bimetallic nanocatalysts have been used for the development of organic reactions, owing to the synergistic effect between the transition metals. A new procedure for synthesizing amines by the reduction of imines with H2 at atmospheric pressure and room te

Large-steric-hindrance N-heterocyclic carbene palladium complex, preparation method and application thereof, and synthesis method of sonidegib based on large-steric-hindrance N-heterocyclic carbene palladium complex

The invention belongs to the technical field of organic synthesis and chemical catalysis, and discloses a large-steric-hindrance N-heterocyclic carbene palladium complex, a preparation method thereof,an application of the complex in efficient catalysis of a C-N coupling reaction under a room-temperature air condition, and a synthesis method of sonidegib based on the complex. According to the large-steric-hindrance N-heterocyclic carbene palladium complex, diphenyl imidazole serves as a main ligand framework, functionalized allyl serves as an auxiliary ligand, the functionalized allyl is introduced beside a metal center of a catalyst to serve as an auxiliary ligand, the catalytic activity and stability are remarkably improved, the large-steric-hindrance N-heterocyclic carbene palladium complex can be applied to efficient catalysis of a CN coupling reaction, particularly, the CN coupling reaction can be efficiently catalyzed under the room temperature condition, and the yield can reachup to 99%. The invention also provides a method for synthesizing sonidegib by taking aryl/aliphatic amine and aryl chloride as reactants and a three-step method at room temperature under the catalysisof a palladium catalytic system, the synthetic method has few steps, and the total yield can reach 74.5%.

Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines

Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.

N-Benzylation of primary amines using magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine as an efficient and recyclable heterogeneous catalyst

Herein we report, a new, simple and mild procedure for N-benzylation and N,N-dibenzylation of anilines through the reaction of aniline derivatives and benzyl bromide at 60 °C in EtOH in the presence of catalytic amounts of magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine (Fe3O4?SiO2?Propyl-HMTA). The title compounds were formed in high purity and their structures characterized by spectral analysis. The results also showed that the magnetic nanoparticle catalyst had significant advantages including, simplicity of preparation, heterogeneity, stability and recyclability. Moreover, the catalyst was characterized by various methods, such as FT-IR, SEM, VSM, TEM, TGA and XRD, after the reaction to compare with its structure before reaction.

Direct electrochemical reductive amination between aldehydes and amines with a H/D-donor solvent

A novel electrochemical synthesis protocol has been achieved for reductive amination between aldehydes and amines in undivided cells at room temperature. Under metal-free and external-reductant-free electrolysis conditions, various important secondary amine products are obtained in moderate-to-high yields. Deuterium-labeling experiments have demonstrated that low-toxicity DMSO acts both as a solvent and a H-donor in the reaction. On this basis, various deuterium-labeled products with good-to-excellent D-incorporation have been synthesized by using DMSO-d6 as a solvent. Furthermore, a molecule with GR-antagonistic activity has been synthesized through further sulfonylation.

Novel N-Substituted Benzomorphan-Based Compounds: From MOR-Agonist/DOR-Antagonist to Biased/Unbiased MOR Agonists

Modifications at the basic nitrogen of the benzomorphan scaffold allowed the development of compounds able to segregate physiological responses downstream of the receptor signaling, opening new possibilities in opioid drug development. Alkylation of the phenyl ring in the N-substituent of the MOR-agonist/DOR-antagonist LP1 resulted in retention of MOR affinity. Moreover, derivatives 7a, 7c, and 7d were biased MOR agonists toward ERK1,2 activity stimulation, whereas derivative 7e was a low potency MOR agonist on adenylate cyclase inhibition. They were further screened in the mouse tail flick test and PGE2-induced hyperalgesia and drug-induced gastrointestinal transit.

Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPentAn complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to CAr-N bond formation under mild conditions without the exclusion of air and moisture.

Oxidative amination of benzylic alkanes with nitrobenzene derivatives as nitrogen sources

The oxidative amination of inert C[sbnd]H bonds has the potential to fundamentally change chemistry but is severely limited by the low chemo- and regio-selectivity under oxidation conditions. Until now, no efficient methodology for the direct intermolecular amination of terminal sp3-C[sbnd]H bonds to N-alkyl amines has existed. Here, a new concept is proposed for the oxidative amination of the terminal sp3-C[sbnd]H bond in alkanes via the construction of a complex reaction system composed of a carbon-supported Co-Ni bimetallic catalyst, an alkane, nitrobenzene, tert-butyl hydroperoxide and hydrogen. This system allows the reduction of nitrobenzene to aniline and the further oxidative amination of the alkane. Nitrobenzene and toluene derivatives can be successfully transformed into the corresponding N-benzyl aniline derivatives with up to 95% isolated yields, and the reaction shows excellent functional group tolerance. This approach offers a new concept for catalyst design and may strongly promote the study of inert C[sbnd]H bond activation and the synthesis of functional N-containing compounds.

Carbon dioxide promoted reductive amination of aldehydes in water mediated by iron powder and catalytic palladium on activated carbon

A mixture of iron powder and catalytic palladium on activated carbon has been developed for reductive amination of various aromatic aldehydes, including 2-pyridinecarboxaldehyde, in water under CO2 atmosphere. The reversible reaction of CO2 with water could form carbonic acid and hydrogen transfer from water to Pd(0) took place with the presence of iron powder, leading to formation of high-active Pd hydrides for the reductive amination process. On the other hand, the reaction system could be inherently neutralized by ready removal of CO2, thus resulting in facile post-processing.

Scalable synthesis of secondary and tertiary amines by heterogeneous Pt-Sn/γ-Al2O3catalyzed N-alkylation of amines with alcohols

Synthesis of secondary and tertiary amines has been efficiently realized from the N-alkylation of amines with alcohols by means of heterogeneous bimetallic Pt-Sn/γ-Al2O3catalyst (0.5?wt % Pt, molar ratio Pt:Sn?=?1:3) through a borrowing hydrogen strategy. The Pt-Sn/γ-Al2O3catalyst has exhibited very high catalytic activity towards a wide range of amines and alcohols, and can be conveniently recycled without Pt metal leaching. The present protocol was applied for the synthesis of N-phenylbenzylamine in 96% isolated yield from aniline and benzyl alcohol on a 2.1?kg scale of the substrates, demonstrating its potential applicability for higher-order amine synthesis.