2449-49-2

Usage

Uses

Used in Organic Synthesis:
N,N-DIMETHYL-1-PHENYLETHYLAMINE is used as a reactant in organic synthesis for the preparation of pharmaceuticals and other fine chemicals. Its unique structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of a wide range of compounds.
Used in Chemical Reactions:
In the chemical industry, N,N-DIMETHYL-1-PHENYLETHYLAMINE serves as a reagent in certain chemical reactions. Its ability to act as a base or a nucleophile contributes to its utility in facilitating specific transformations and processes.
Used as a Precursor:
N,N-DIMETHYL-1-PHENYLETHYLAMINE is also used as a precursor to other organic compounds. Its functional groups and structural features make it a suitable starting material for the synthesis of more complex molecules, which can be further utilized in various applications.
Used in Research:
Due to its psychoactive properties and potential as a mild stimulant, N,N-DIMETHYL-1-PHENYLETHYLAMINE is used in research to study the effects on the central nervous system. This research can help in understanding its mechanism of action and potential therapeutic applications, while also informing safety measures for its use.

InChI:InChI=1/C10H15N/c1-9(11(2)3)10-7-5-4-6-8-10/h4-9H,1-3H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 827-36-1 2-(N,N-dimethylamino)-2-phenylacetonitrile 
• 50-00-0 formaldehyd 
• 618-36-0 rac-methylbenzylamine 
• 5350-67-4 α-(dimethylamino)-propionitrile 
• 5350-41-4 trimethylbenzylammonium bromide 
• 591-51-5 phenyllithium 
• 68-12-2 N,N-dimethyl-formamide 
• 98-86-2 acetophenone 
• 21478-66-0 (chloromethyl)-trimethylammonium chloride 
• 60779-09-1 1-phenylethylmagnesium chloride 
• 85506-17-8 (2R,4S,5R)-2-O-(N,N-dimethylhydroxylamino)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 
• 67-56-1 methanol 

Downstream Products

• 42142-07-4 dimethyl-(1-phenyl-ethyl)-amine oxide 
• 96990-21-5 Hexadecyl-dimethyl-(1-phenyl-ethyl)-ammonium; bromide 
• 122571-79-3 α-methyl-N,N-dimethyl-2-hydroxymethylbenzylamine 
• 866953-73-3 (dirhodium(II) tetratrifluoroacetate)*(N,N-dimethyl-1-phenylethylamine) 
• 1265226-32-1 o-(Mes₂B)C₆H₄CH(Me)NMe₂ 
• 1265226-31-0 (C6F5)2B(α-methylbenzyl(N,N-dimethyl)amine(-H)) 
• 1265226-30-9 Cy2B(α-methylbenzyl(N,N-dimethyl)amine(-H)) 
• 24422-69-3 (1-phenylethyl)(4-methylphenyl)sulfide 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Preparation method of N-alkylated derivative of primary amine compound

The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate

The base-induced Sommelet–Hauser (S–H) rearrangement of N-(α-branched)benzylic glycine ester-derived ammonium salts 1 was investigated. When the α-branched substituent was a simple alkyl, such as a methyl or butyl, desired S–H rearrangement product 2 was obtained in low yield with formation of the [1,2] Stevens rearranged 4 and Hofmann eliminated products 5 and 6. However, when the α-branched substituent had a 2-oxy moiety, such as 2-acetoxyethyl or 2-benzoyloxyethyl, the yields of 2 were improved. These results could be explained by formation of chelated intermediate C that stabilizes the carbanionic ylide, and the subsequent initial dearomative [2,3] sigmatropic rearrangement would be accelerated. The existence of C was supported by mechanistic experiments. This enhancement effect is not very strong or effective; however, it will expand the synthetic usefulness of ammonium ylide rearrangements.

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates

A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst

The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.

Methyl-Selective α-Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN-AZADO or 1-Me-AZADO)

Methyl-selective α-oxygenation of tertiary amines is a highly attractive approach for synthesizing formamides while preserving the amine substrate skeletons. Therefore, the development of efficient catalysts that can advance regioselective α-oxygenation at the N-methyl positions using molecular oxygen (O2) as the terminal oxidant is an important subject. In this study, we successfully developed a highly regioselective and efficient aerobic methyl-selective α-oxygenation of tertiary amines by employing a Cu/nitroxyl radical catalyst system. The use of moderately hindered nitroxyl radicals, such as 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO) and 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO), was very important to promote the oxygenation effectively mainly because these N-oxyls have longer life-times than less hindered N-oxyls. Various types of tertiary N-methylamines were selectively converted to the corresponding formamides. A plausible reaction mechanism is also discussed on the basis of experimental evidence, together with DFT calculations. The high regioselectivity of this catalyst system stems from steric restriction of the amine-N-oxyl interactions.

Mechanistic Studies on the Nickel-Catalyzed Cyclopropanation with Lithiomethyltrimethylammonium Triflate

We report here our mechanistic study of the previously published nickel-catalyzed cyclopropanation reaction using lithiomethyltrimethylammonium triflate as methylene donor. The cyclopropane yield is highly dependent on the olefin substrate and correlates well with the binding affinity of the olefin to Ni(0) as established elsewhere. On the basis of this observation, we developed a simplified mechanistic model that can explain several odd observations we found in our initial report. Most importantly, a binding equilibrium between the olefin substrate and phosphine ligand appears to govern the ratio between product formation and unproductive ylide decomposition in a side reaction.

Method for synthesizing methylated aliphatic amine compound

The invention discloses a method for synthesizing a methylated aliphatic amine compound. A commercially available or easily synthesized aliphatic amine, adopted as a raw material, is subjected to a methylation reaction with methanol to obtain the methylated aliphatic amine compound. The reaction is performed in the presence of an iridium metal complex and under weak alkaline catalysis conditions,only a N,N-dimethylated product is produced without generation of a monomethyl product so that selectivity is high, produced byproduct is water only so that no harm to the environment is caused, and the atom economy of the reaction is high, and therefore, the method meets the requirements of green chemistry and has a broad development prospect.