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Cas Database

191869-65-5

191869-65-5

Identification

  • Product Name:4-((methyl(phenylmethyl)amino)methyl)benzonitrile

  • CAS Number: 191869-65-5

  • EINECS:

  • Molecular Weight:236.316

  • Molecular Formula: C16H16N2

  • HS Code:

  • Mol File:191869-65-5.mol

Synonyms:4-((methyl(phenylmethyl)amino)methyl)benzonitrile

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Relevant articles and documentsAll total 7 Articles be found

Regio- and chemoselective Csp3-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis

Ide, Takafumi,Barham, Joshua P.,Fujita, Masashi,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka

, p. 8453 - 8460 (2018)

We present a highly regio- and chemoselective Csp3-H arylation of benzylamines mediated by synergy of single electron transfer (SET) and hydrogen atom transfer (HAT) catalysis. Under well precedented SET catalysis alone, the arylation reaction of N,N-dimethylbenzylamine proceeded via aminium radical cation formation and selectively targeted the N-methyl group. In contrast, addition of PhC(O)SH as a HAT catalyst precursor completely switched the regioselectivity to Csp3-H arylation at the N-benzylic position. Measurement of oxidation potentials indicated that the conjugate base of PhC(O)SH is oxidized in preference to the substrate amine. The discovery of the thiocarboxylate as a novel HAT catalyst allowed for the selective generation of the sulfur-centered radical, so that the N-benzyl selectivity was achieved by overriding the inherent N-methyl and/or N-methylene selectivity under SET catalysis conditions. While visible light-driven α-C-H functionalization of amines has mostly been demonstrated with aniline derivatives and tetrahydroisoquinolines (THIQs), our method is applicable to a variety of primary, secondary and tertiary benzylamines for efficient N-benzylic C-H arylation. Functional group tolerance was high, and various 1,1-diarylmethylamines, including an α,α,α-trisubstituted amine, were obtained in good to excellent yield (up to 98%). Importantly, the reaction is applicable to late-stage functionalization of pharmaceuticals.

Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol

Ai, Yao,Chen, Xiaozhong,Li, Feng,Liu, Peng,Yang, Chenchen,Yang, Jiazhi

, p. 325 - 334 (2021/10/07)

A Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand was designed, synthesized, and found to be a general and efficient auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol as both hydrogen source and methylating reagent. In the presence of [Cp*Ir(2,2′-CH2BiBzImH2)Cl][Cl], a range of desirable products were obtained in high yields with nearly complete selectivities. The reaction is highly attractive due to the highly atom economy, and minimal consumption of chemicals and energy. Notably, this research exhibits new potential of metal–ligand bifunctional catalysts for the activation of methanol as C1 source for organic synthesis.

Late-Stage N-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis

Shen, Yangyang,Rovis, Tomislav

supporting information, p. 16364 - 16369 (2021/10/21)

The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of various trialkylamines. Our catalytic system shows exclusive N-Me selectivity with a wide range of trialkylamines under mild conditions, even in the context of late-stage arylation of pharmaceutical compounds bearing this common structural motif. Mechanistic studies indicate the unconventional behavior of Ni catalyst upon intercepting the α-amino radicals, in which only the primary α-amino radical undergoes a successful cross-coupling process.

New melatonin- N, N -dibenzyl(N -methyl)amine hybrids: Potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for alzheimers disease

López-Iglesias, Beatriz,Pérez, Concepción,Morales-García, José A.,Alonso-Gil, Sandra,Pérez-Castillo, Ana,Romero, Alejandro,López, Manuela G.,Villarroya, Mercedes,Conde, Santiago,Rodríguez-Franco, María Isabel

, p. 3773 - 3785 (2014/05/20)

Here, we describe a new family of melatonin-N,N-dibenzyl(N-methyl)amine hybrids that show a balanced multifunctional profile covering neurogenic, antioxidant, cholinergic, and neuroprotective properties at low-micromolar concentrations. They promote maturation of neural stem cells into a neuronal phenotype and thus they could contribute to CNS repair. They also protect neural cells against mitochondrial oxidative stress, show antioxidant properties, and inhibit human acetylcholinesterase (AChE). Moreover, they displace propidium from the peripheral anionic site of AChE, preventing the β-amyloid aggregation promoted by AChE. In addition, they show low cell toxicity and can penetrate into the CNS. This multifunctional profile highlights these melatonin-N,N-dibenzyl(N-methyl)amine hybrids as useful prototypes in the research of innovative drugs for Alzheimers disease.

Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238

Rizzo, Stefano,Bartolini, Manuela,Ceccarini, Luisa,Piazzi, Lorna,Gobbi, Silvia,Cavalli, Andrea,Recanatini, Maurizio,Andrisano, Vincenza,Rampa, Angela

experimental part, p. 1749 - 1760 (2010/05/17)

We report on a series of hybrid compounds structurally derived from donepezil and AP2238. This study was aimed at improving the activities of the reference compounds, donepezil and AP2238, and at broadening the range of activities of new derivatives as, due to the multifactorial nature of AD, molecules that modulate the activity of a single protein target are unable to significantly modify the progression of the disease. In particular, the indanone core from donepezil was linked to the phenyl-N-methylbenzylamino moiety from AP2238, through a double bond that was kept to evaluate the role of a lower flexibility in the biological activities. Moreover, SAR studies were performed to evaluate the role of different substituents in position 5 or 6 of the indanone ring in the interaction with the PAS, introducing also alkyl chains of different lengths carrying different amines at one end. Derivatives 21 and 22 proved to be the most active within the series and their potencies against AChE were in the same order of magnitude of the reference compounds. Compounds 15, 21-22, with a 5-carbon alkyl chain bearing an amino moiety at one end, better contacting the PAS, remarkably improved the inhibition of AChE-induced Aβ aggregation with respect to the reference compounds. They also showed activity against self-aggregation of Aβ42 peptide, the most amyloidogenic form of amyloid produced in AD brains, while the reference compounds resulted completely ineffective.

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

4‐[benzyliminomethyl]benzonitrile
67907-57-7

4‐[benzyliminomethyl]benzonitrile

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
With C25H27ClIrN4(1+)*Cl(1-); caesium carbonate; at 125 ℃; for 12h; Schlenk technique;
80%
N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; sodium carbonate; In 1,4-dioxane; at 28 ℃; for 18h; Inert atmosphere; Glovebox; Irradiation;
82%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
In tetrahydrofuran; diethyl ether; 4-cyanobenzyl bromide;
In tetrahydrofuran; diethyl ether; 4-cyanobenzyl bromide;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
In toluene; for 8h; Reflux;
64%
In diethyl ether; for 10h; Reflux;
terephthalonitrile
623-26-7

terephthalonitrile

N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>

C16H16N2

Conditions
Conditions Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); In N,N-dimethyl acetamide; at 20 ℃; for 12h; Reagent/catalyst; regioselective reaction; Mechanism; Irradiation;
10 %Spectr.
85 %Spectr.
methanol
67-56-1

methanol

4‐[benzyliminomethyl]benzonitrile
67907-57-7

4‐[benzyliminomethyl]benzonitrile

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
With C25H27ClIrN4(1+)*Cl(1-); caesium carbonate; at 125 ℃; for 12h; Schlenk technique;
80%
N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; sodium carbonate; In 1,4-dioxane; at 28 ℃; for 18h; Inert atmosphere; Glovebox; Irradiation;
82%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
In tetrahydrofuran; diethyl ether; 4-cyanobenzyl bromide;
In tetrahydrofuran; diethyl ether; 4-cyanobenzyl bromide;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

Conditions
Conditions Yield
In toluene; for 8h; Reflux;
64%
In diethyl ether; for 10h; Reflux;
terephthalonitrile
623-26-7

terephthalonitrile

N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

4-((methyl(phenylmethyl)amino)methyl)benzonitrile
191869-65-5

4-((methyl(phenylmethyl)amino)methyl)benzonitrile

C<sub>16</sub>H<sub>16</sub>N<sub>2</sub>

C16H16N2

Conditions
Conditions Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); In N,N-dimethyl acetamide; at 20 ℃; for 12h; Reagent/catalyst; regioselective reaction; Mechanism; Irradiation;
10 %Spectr.
85 %Spectr.

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