34160-43-5

Upstream product

• 51488-27-8 N-(4-methylcyclohexylidene)pyridine-3-amine 
• 62-53-3 aniline 
• 589-92-4 1-methylcyclohexan-4-one 
• 589-91-3 p-methylcyclohexanol 
• 108-94-1 cyclohexanone 

Downstream Products

• 620-84-8 4-methyldiphenylamine 
• 86822-65-3 trans-N-cyclohexyl-4-methylcyclohexylamine 
• 766463-66-5 cis-N-cyclohexyl-4-methylcyclohexylamine 
• 20440-95-3 N-phenyl-di-p-tolylamine 

Relevant academic research and scientific papers

Efficient One-Pot Reductive Aminations of Carbonyl Compounds with Aquivion-Fe as a Recyclable Catalyst and Sodium Borohydride

A one-pot reductive amination of aldehydes and ketones with NaBH4 was developed with a view to providing efficient, economical and greener synthetic conditions. A recyclable iron-based Lewis catalyst, Aquivion-Fe, was used to promote imine formation in cyclopentyl methyl ether, followed by the addition of a small amount of methanol to the reaction mixture to enable C=N reduction by NaBH4. The protocol, applied to a wide number of amines and carbonyl compounds, resulted in ever complete conversion of these latter with excellent chemoselectivity towards the expected amination products in the most cases. Isolated yields, determined for a selection of the screened substrates, were found consistent with the previously obtained conversion and selectivity data. Cinacalcet, an important active pharmaceutical ingredient, was efficiently prepared by the title procedure.

Design, Synthesis, and Structure-Activity Relationship Studies of Novel Indolyalkylpiperazine Derivatives as Selective 5-HT1A Receptor Agonists

5-HT1A receptor (5-HT1AR) agonists have been implicated in the treatment of a variety of central nervous system (CNS) diseases such as depression and anxiety, et al. Based on our previously found compound FW01 (Ki = 51 ± 16 nM) obtained by virtual screening, a series of FW01 derivatives were designed and synthesized by the modification of the amide tail group as well as indole headgroup of FW01. SAR exploration found that amide tail group and indole headgroup play pivotal roles in determining the binding affinity and selectivity on dopamine and serotonin receptor subtypes. Among all tested compounds, 9_24 has a Ki value of 5 ± 0.6 nM with a good selectivity toward 5-HT1AR. The [35S] GTPγS assay showed that 9_24 is a full agonist toward 5-HT1AR with an EC50 value of 0.059 nM, which shows 266.2 and 146.4-fold selectivity to 5-HT2A and D3 respectively. Molecular dynamics simulations and molecular docking studies with 5-HT1AR-9_24 were performed to disclose the mechanism of its high activity and selectivity. Finally, a detailed stepwise 9_24 induced signal transduction mechanism of 5-HT1AR is proposed.

Band-Gap Narrowing of Highly Stable Heterogeneous ZrO2–ZnO Nanocomposites for the Reductive Amination of Carbonyl Compounds with Formic Acid and Triethylamine

The band gap of a material can be affected by factors such as size, doping materials, and oxygen vacancies. The decrease in band gap and change in state of ZrO2 with the addition of ZnO indicates interfacial interactions between ZrO2 and ZnO in the nanocomposites (NCs), which is further confirmed by the observed shift of the peaks in the Raman spectra. Heterobimetallic ZrO2–ZnO NCs were synthesized through a sustainable green approach by using sucrose isolated from Angelica gigas Nakai root extract. The highly stable NCs displayed excellent catalytic activity for reductive amination of carbonyl compounds utilizing HCO2H/(CH3CH2)3N as a hydrogen source. The high catalytic performance of the NCs was closely correlated with the narrow band gap and synergistic effect of ZrO2 with ZnO in the NCs.

Selective Synthesis of Primary Anilines from NH3 and Cyclohexanones by Utilizing Preferential Adsorption of Styrene on the Pd Nanoparticle Surface

Dehydrogenative aromatization is one of the attractive alternative methods for directly synthesizing primary anilines from NH3 and cyclohexanones. However, the selective synthesis of primary anilines is quite difficult because the desired primary aniline products and the cyclohexanone substrates readily undergo condensation affording the corresponding imines (i.e., N-cyclohexylidene-anilines), followed by hydrogenation to produce N-cyclohexylanilines as the major products. In this study, primary anilines were selectively synthesized in the presence of supported Pd nanoparticle catalysts (e.g., Pd/HAP, HAP=hydroxyapatite, Ca10(PO4)6(OH)2) by utilizing competitive adsorption unique to heterogeneous catalysis; in other words, when styrene was used as a hydrogen acceptor, which preferentially adsorbs on the Pd nanoparticle surface in the presence of N-cyclohexylidene-anilines, various structurally diverse primary anilines were selectively synthesized from readily accessible NH3 and cyclohexanones. The Pd/HAP catalyst was reused several times though its catalytic performance gradually declined.

CuI nanoparticles as recyclable heterogeneous catalysts for C-N bond formation reactions

Herein, copper iodide nanoparticles (NPs) are reported for the reductive amination of carbonyl compounds for the first time. The generated NPs were characterized by TEM, EDX, XRD and XPS analyses. The XRD patterns, XPS, and EDX analysis confirmed that the resulting NPs were CuI instead of Cu. The TEM images of CuI exhibited the size of monodispersed spherical NPs in the range of 4 ± 2 nm. These generated NPs can be used as versatile heterogeneous catalysts for important organic transformations. As a proof of concept, CuI NPs were successfully applied as heterogeneous catalysts for the synthesis of secondary amines, amides and triazoles. CuI NPs can be easily recovered and recycled up to six times.

Higher-Affinity Agonists of 5-HT1AR Discovered through Tuning the Binding-Site Flexibility

Discovery of high-affinity and high-selectivity agonists of 5-HT1AR has become very attractive due to their potential therapeutic effects on multiple 5-HT1AR-related psychological and neurological problems. On the basis of our previously designed lead compound FW01 (Ki = 51.9 nM, denoted as 9a in the present study), we performed large-scale molecular dynamics simulations and molecular docking operations on 5-HT1AR-9a binding. We found the flip-packing events for the headgroup of 9a, and we also found that its tail group could bind flexibly at the agonist-binding site of 5-HT1AR. By finely tuning the flip-packing phenomenon of the 9a headgroup and tuning the binding flexibility of 9a tail group, we virtually designed a series of new 9a derivatives through molecular docking operations and first-principles calculations and predicted that these newly designed 9a derivatives should be higher-affinity agonists of 5-HT1AR. The computational predictions on the new 9a derivatives have been confirmed by our wet-experimental studies as chemical synthesis, binding affinity assays, and agonistic-function assays. The consistency between our computational design and wet-experimental measurements has led to our discovery of higher-affinity agonists of 5-HT1AR, with ～50-fold increase in receptor-binding affinity and ～25-fold improvements in agonistic function. In addition, our newly designed 5-HT1AR agonists showed very high selectivity of 5-HT1AR over subtype 5-HT2AR and also over three subtypes of dopamine receptors (D1, D2, and D3). (Graph Presented).

Cobalt(II) phthalocyanine-catalyzed highly chemoselective reductive amination of carbonyl compounds in a green solvent

Cobalt phthalocyanine has been employed for the highly chemoselective reductive amination of aldehydes and ketones in ethanol as a green solvent. A large range of functional groups such as nitro, acid, amide, ester, nitrile, halogen, lactone, methoxy, hydroxy, alkene, N-benzyl, O-benzyl and heterocyclic rings were well tolerated under the present reaction conditions. Copyright

Reductive amination of aldehydes and ketones with sodium borohydride supported onto HZSM-5 zeolite under microwave irradiation in a solvent free system

Sodium borohydride supported onto a HZSM-5 zeolite is presented as a general reducing agent for the reductive amination of aldehydes and ketones under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.

Catalytic Synthesis of Triarylamines

Condensation along Ullman reaction in the presence of copper catalysts was carried out with para-substituted arylamines and p-iodotoluene to yield the corresponding triarylamines. For preparation of diarylamines was used dehydrogenation of N-cycloalkylanilines and azomethines; diarylamines were obtained through dehydroamination of cycloaliphatic alcohols with anilines.