55096-85-0

Usage

General Description

Benzenemethanamine,4-(dimethylamino)-N-(phenylmethyl)-, also known by its common name, N,N-dimethyl-1-phenylmethanamine, is a chemical compound with a molecular formula C16H20N2. It is often used as a precursor in the production of pharmaceuticals, and as a reagent in the synthesis of organic compounds. Benzenemethanamine,4-(dimethylamino)-N-(phenylmethyl)- has a range of applications, including as an intermediate in the synthesis of medications such as vasopressors, local anesthetics, and antihypertensives. It is also used in the manufacturing of dyes and pigments, and as a corrosion inhibitor in various industries. Overall, Benzenemethanamine,4-(dimethylamino)-N-(phenylmethyl)- is a versatile and important chemical compound with various industrial uses.

InChI:InChI=1/C16H20N2/c1-18(2)16-10-8-15(9-11-16)13-17-12-14-6-4-3-5-7-14/h3-11,17H,12-13H2,1-2H3/p+1

Upstream product

• 100-52-7 benzaldehyde 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 100-46-9 benzylamine 
• 108191-13-5 N-benzyl-[4-(N,N-dimethylamino)]-benzamide 
• 1384953-85-8 C₂₀H₃₀N₂Si 
• 24431-17-2 N-(p-dimethylaminobenzylidene)benzylamine 

Downstream Products

• 133102-34-8 benzyl-(4-dimethylamino-benzyl)-nitroso-amine 
• 55097-38-6 N¹-Benzyl-N¹-(4-dimethylamino-benzyl)-pentane-1,5-diamine 
• 101268-80-8 4-[(N-benzyl-hydrazino)-methyl]-N,N-dimethyl-aniline 

Relevant academic research and scientific papers

Nickel-Catalyzed Reduction of Secondary and Tertiary Amides

The nickel-catalyzed reduction of secondary and tertiary amides to give amine products is reported. The transformation is tolerant of extensive variation with respect to the amide substrate, proceeds in the presence of esters and epimerizable stereocenters, and can be used to achieve the reduction of lactams. Moreover, this methodology provides a simple tactic for accessing medicinally relevant α-deuterated amines.

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).

Heterogeneous Catalytic Reductive Amination of Carbonyl Compounds with Ni-Al Alloy in Water as Solvent and Hydrogen Source

The heterogeneous catalytic reductive amination of carbonyl compounds has been achieved by reactions of ammonium hydroxide and various amines with ketones and aldehydes. The process is based on the application of Raney type Ni-Al alloy in an aqueous medium. The reaction of the carbonyl compounds with the amine provided the corresponding Schiff bases that immediately underwent a reduction to provide primary and secondary amines as products. The controlled reaction of the Al content of the alloy with the solvent water generates hydrogen, and the in situ formed Raney Ni serves as a hydrogenation catalyst. The method is a simple and efficient way of preparing a broad variety of primary and secondary amines.

Graphene-supported NiPd alloy nanoparticles: A novel and highly efficient heterogeneous catalyst system for the reductive amination of aldehydes

A novel and highly efficient heterogeneous catalytic reductive amination of aldehydes is described. The recently developed graphene supported NiPd alloy nanoparticle (G-NiPd) catalyst using ammonia borane (AB) as a green, stable and safe hydrogen donor was used in a water/methanol mixture (v/v = 2/3) under ambient conditions. The catalytic system was successfully applied in the reductive amination of various substituted aldehydes with amines and the corresponding products were obtained in (up to) 99% yield in 6 h. The G-NiPd catalyst could be recycled up to five times without any significant loss in the product yield.

Trisubstituted sulfonamides: A new chemotype for development of potent and selective CB2 receptor inverse agonists

An extensive exploration of the structure-activity relationship of a trisubstituted sulfonamide series led to the identification of 39, which is a potent and selective CB2 receptor inverse agonist [K i(CB2) = 5.4 nM, and Ki(CB1) = 500 nM]. The functional properties measured by cAMP assays indicated that the selected compounds were CB2 inverse agonists with high potency values (for 34, EC50 = 8.2 nM, and for 39, EC50 = 2.5 nM). Furthermore, an osteoclastogenesis bioassay indicated that trisubstituted sulfonamide compounds showed great inhibition of osteoclast formation.

TERTIARY AMINES FOR USE IN THE TREATMENT OF CARDIAC DISORDERS

The present invention relates to tertiary amines of formula (I) for use in therapy, particularly for use in treating cardiovascular disorders. The compounds have been found to regulate phospholamban phosphorylation by interfering with the A-kinase anchor protein 18delta (AKAP185) binding to the PKA substrate phospholamban. The compounds share a tri(alkylaryl/alkylheteroaryl) amine structure.

Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane

Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE) 2Cl]2 with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.

Direct reductive amination of aldehydes using lithium-arene(cat.) as reducing system. A simple one-pot procedure for the synthesis of secondary amines

A simple one-pot procedure for the direct reductive amination of aldehydes using lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) or a polymer supported naphthalene as reducing system is described. The direct reductive amination of a variety of aldehydes with primary amines was achieved simply by adding a mixture of the corresponding carbonyl compound and the amine, over a solution of the lithium arenide in THF at room temperature. For most of the substrates tested the main reaction products were the secondary amines along with variable amounts of the corresponding alcohol and/or imine products. Theoretical DFT calculations have been applied in order to explain the differences in reactivity observed for aromatic substrates.