82363-30-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(3,4-DIMETHOXY-BENZYL)-PHENYL-AMINE is used as a building block in the production of complex organic molecules, particularly in the synthesis of pharmaceuticals. Its unique structure allows it to be a key component in creating a wide range of medicinal compounds.
Used in Organic Compound Synthesis:
In the field of organic chemistry, (3,4-DIMETHOXY-BENZYL)-PHENYL-AMINE is used as a reagent in chemical reactions. Its reactivity contributes to the formation of various organic compounds, making it a versatile tool for chemists.
Used in Medicinal Chemistry and Drug Discovery:
(3,4-DIMETHOXY-BENZYL)-PHENYL-AMINE also has potential applications in the field of medicinal chemistry and drug discovery. As a precursor in the synthesis of potential drug candidates, it plays a crucial role in the development of new therapeutic agents.
Used in Chemical Reactions:
Furthermore, (3,4-DIMETHOXY-BENZYL)-PHENYL-AMINE is utilized as a reagent in various chemical reactions, facilitating the synthesis of a broad spectrum of chemical products, which can be applied across different industries.

Upstream product

• 27895-67-6 N-(3,4-dimethoxybenzylidene)aniline 
• 62-53-3 aniline 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 106-49-0 p-toluidine 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 98-80-6 phenylboronic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 98-95-3 nitrobenzene 
• 114468-29-0 (E)-1-(3,4-dimethoxyphenyl)-N-phenylmethanimine 

Downstream Products

• 27895-67-6 N-(3,4-dimethoxybenzylidene)aniline 
• 1295581-89-3 N-(3,4-dimethoxybenzyl)-N-phenethylaniline 
• 1295581-88-2 N-benzyl-N-(3,4-dimethoxybenzyl)aniline 

Relevant academic research and scientific papers

Boron-containing capsaicinoids

This study reports on the preparation of eight new boron-containing capsaicinoids bearing long aliphatic chains, as an expansion of our previous studies to include tertiary amide derivatives into our substrate scope. Our boron-moiety, a pinacolboronate es

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

Ru(II)-NHC catalysed N-Alkylation of amines with alcohols under solvent-free conditions

The reaction of [RuCl2(p-cymene)]2 with in situ prepared Ag-N-heterocyclic carbene (NHC) complexes yields a series of [RuCl2(p-cymene)(NHC)] complexes (2). All of the complexes have been characterised by elemental analysis, and 1H NMR and 13C NMR spectroscopies. These complexes have been tested for the N-alkylation of aromatic amines with arylmethyl alcohols under neat conditions in the presence of KOtBu at 120 °C. Compounds (2) are stable and have high catalytic/selective activity for the N-alkylation reactions of primary amines to afford secondary amines.

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.

First used of Alkylbenzimidazole-Cobalt(II) complexes as a catalyst for the N-Alkylation of amines with alcohols under solvent-free medium

In this study, alkylbenzimidazole-cobalt(II)-catalyzed direct N-alkylation reactions of amines with alcohols derivatives have been investigated under solvent-free medium. For this purpose, a series of cobalt(II) complexes bearing N-alkylbenzimidazole complexes have been synthesized and novel complexes fully characterized by elemental analysis, FT-IR, 1H NMR and, 13C{1H} NMR spectroscopies. Also, the structure of the complex 2a has been confirmed by X-ray crystallography. Generally, the N-alkylating reaction is usually performed in toluene with various metal complexes including cobalt. In this catalytic study of complexes, 2a-c has carried out in without solvent and alcohol acted both as solvent and reactant. Conversion and selectivity of amine products according to imine products for alkylation reactions have been seen high yield in medium solvent-free relative to in toluene.

Novel N-Alkylbenzimidazole-Ruthenium (II) complexes: Synthesis and catalytic activity of N-alkylating reaction under solvent-free medium

In this article, direct N-alkylation reactions of amines with alcohols derivatives have been investigated. For this purpose, a new series ruthenium (II) complexes bearing N-coordinated benzimidazole complexes with have been synthesized and fully characterized by elemental analysis, FT-IR, 1H NMR and, 13C NMR spectroscopies. Additionally, the structures of the complexes 2b and 2c have been confirmed by X-ray crystallography. Although the N-alkylating reaction is usually performed in toluene, the catalytic study of complexes 2a-d has carried out no additional solvent and alcohol acted both as solvent and reactant of alkylating by using a little excess of alcohols. Surprisingly, conversion and selectivity of amine product for alkylation reaction have been seen high in medium solvent-free relative to in toluene.

Well-Defined Amidate-Functionalized N-Heterocyclic Carbene -Supported Rare-Earth Metal Complexes as Catalysts for Efficient Hydroboration of Unactivated Imines and Nitriles

Four amidate-functionalized N-heterocyclic carbene (NHC) rare-earth metal amido complexes [(κ2-N,O-κ1-L)2REN(SiMe3)2] (L = 1-(C6H5CONCH2CH2)-3-(CH3)3C6H2(N(CH)2NC)) [RE = Er (1), Y (2), Dy (3), Gd (4)] were synthesized by one-pot reactions of 2 equiv of (1-(C6H5CONHCH2CH2)-3-(CH3)3C6H2-(N(CH)2NCH))Br (H2LBr) with 5 equiv of KN(SiMe3)3 followed by treatment with 1 equiv of RECl3 in tetrahydrofuran at -40 °C. These complexes were fully characterized, and their catalytic activities toward hydroboration of unactivated imines and nitriles were investigated, and it was found that these complexes displayed excellent activities as well as remarkable functional group compatibility for imine and nitrile substrates such as halo-, alkyl-, hydroxyl-, N,N-dimethylamino-, and nitro- substituents. Among those, the chemoselectivity for this reaction among the common unsaturated functional groups was achieved in the order CO CN > C=N > CO2Et > CC in the current catalytic system, which may facilitate their further application in synthetic chemistry.

Ruthenium(II)-(p-cymene)-N-Heterocyclic Carbene Complexes for the N-Alkylation of Amine Using the Green Hydrogen Borrowing Methodology

Six ruthenium(II) complexes with the general molecular formula [RuCl2(NHC)(η6-p-cymene)] (NHC = N-heterocyclic carbene) were synthesized by the transmetalation method from [RuCl2(η6-p-cymene)]2 and silver(I)-NHC complexes. All complexes were fully characterized by analytical and spectral methods (FT-IR, elemental analysis and 1H and 13C NMR). The solid-state structure of one of the ruthenium complexes [dichloro-{1-[2-(2-ethoxyphenoxy)ethyl]-3-(3,5-dimethylbenzyl)benzimidazol-2-ylidene}(p-cymene) ruthenium(II)] has been established by single-crystal X-ray diffraction study, which revealed that the ruthenium atom adopt a classical piano-stool coordination geometry. Under the optimised conditions, these ruthenium complexes were found to be efficient catalysts for N-alkylation of aniline with arylmethyl alcohols using the hydrogen borrowing strategy, which is a cost-effective and environmentally attractive reaction for the preparation of N-alkylated amines.

AuPd?Fe3O4 Nanoparticle Catalysts for Highly Selective, One-Pot Cascade Nitro-Reduction and Reductive Amination

Exceedingly chemoselective preparation of secondary amines from the cascade reaction of nitro reduction followed by reductive amination of the resulting amine with an aldehyde through the use of bimetallic AuPd alloy nanoparticle catalyst is described. We prepared a AuPd alloy nanocatalyst supported on Fe3O4 in gram scale without calcination. One pot synthesis of a number of secondary amines was achieved from a variety of nitroarenes and aryl or alkyl aldehydes under 1 atm of H2 at room temperature. No N-debenzylation was observed in the case of the reactions involving aryl aldehydes, which is often observed in the reductive amination catalysed by a transition metal catalyst such as palladium. We also accomplished efficient one-pot synthesis of a number of N-aryl substituted isoindolinone derivatives from 1-formylbenzoic acid and several nitroarenes using the same reaction conditions. Furthermore, thanks to the magnetic property of the Fe3O4 support, the AuPd?Fe3O4 NPs could be easily separated and reused up to 20 times without the loss of its catalytic activity. (Figure presented.).

Air Stable Iron(II) PNP Pincer Complexes as Efficient Catalysts for the Selective Alkylation of Amines with Alcohols

A series of well-defined iron(II) complexes of the types [Fe(PNP)Br2] and [Fe(PNP)(CO)Br2] with PNP pincer ligands based on triazine and pyridine backbones were prepared and fully characterized. These complexes were tested as catalysts for the alkylation of amines by alcohols. The high-spin complexes [Fe(PNP)Br2] are catalytically inactive. The low-spin complexes [Fe(PNP)(CO)Br2] bearing a carbonyl co-ligand efficiently and selectively convert primary alcohols and aromatic and benzylic amines selectively into mono-N-alkylated amines in good to excellent isolated yields. A mechanistic proposal is given. (Figure presented.).