17972-08-6

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 74-89-5 methylamine 
• 593-51-1 methylamine hydrochloride 
• 873-32-5 2-Chlorobenzonitrile 
• 90717-17-2 (±)-(2-chlorophenyl)(1-hydroxycyclopentyl)methanone 
• 6740-87-0 1-((2-chlorophenyl)(methylimino)methyl)cyclopentan-1-ol 
• 6740-85-8 (2-chlorophenyl)(cyclopentyl)methanone 
• 94-64-4 N-methyl-N-(2-chlorobenzyl)amine 

Downstream Products

• 1191057-89-2 (R)-N-(cyano(4-fluorophenyl)methyl)-N-methylacetamide 
• 1191057-91-6 (R)-N-((2-chlorophenyl)(cyano)methyl)-N-methylacetamide 
• 1191057-93-8 (R)-N-(cyano(2,4-difluorophenyl)methyl)-N-methylacetamide 
• 66308-06-3 (2-Chloro-phenyl)-methylamino-acetonitrile 
• 100709-36-2 (2-chloro-benzhydryl)-methyl-amine; hydrochloride 
• 94-64-4 N-methyl-N-(2-chlorobenzyl)amine 
• 1144106-36-4 C₁₂H₁₂ClNO 
• 1262325-06-3 4-(2-chlorobenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one 
• 139215-19-3 9-(2-chlorophenyl)-1,2-dihydro-3H,9H-pyrazolo<1,2-a>-indazol-3-one 

Relevant academic research and scientific papers

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Expedient preparation of active pharmaceutical ingredient ketamine under sustainable continuous flow conditions

A robust three-step continuous flow procedure is presented for the efficient and sustainable preparation of active pharmaceutical ingredient ketamine. The procedure relies on the main assets of continuous flow processing, starts from commercially available chemicals, utilizes low toxicity reagents and a FDA class 3 solvent under intensified conditions. The procedure features a unique hydroxylation step with molecular oxygen, a fast imination relying on triisopropyl borate and a thermolysis employing Montmorillonite K10 as a heterogeneous catalyst, all three steps being performed in ethanol. The three individual steps can be run independently or can be concatenated, thus providing a compact yet efficient setup for the production of ketamine. The scalability of the critical hydroxylation step was assessed in a commercial pilot continuous flow reactor. The process can also be adapted for the preparation of ketamine analogs. A thorough computational study on the backbone rearrangement of the cyclopentylphenylketone scaffold under thermal stress rationalizes the experimental selectivity and the various experimental observations reported herein.

Mechanosynthesis of N-methyl imines using recyclable imidazole-based acid-scavenger: In situ formed ionic liquid as catalyst and dehydrating agent

1,1′-(1,4-Butanediyl)bis(imidazole) was prepared by a modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional condensation reaction with ecological benefits and convenience of a facile mechanosynthetic process. The current method has advantages such as reduced waste by avoiding solvent, exclusion of hazardous materials during the reaction, elimination of handling an anhydrous gas in an evacuated container or a solution of methylamine in ethanol, good yields for relatively unreactive benzaldehydes containing electron-donating substituents, short reaction times, and metal- and acid-free conditions. Furthermore, the promoter was easily regenerated and reused several times with no significant loss of activity.

Method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in presence of visible light

The invention belongs to the technical field of chemical engineering and pharmaceutical industry, and particularly relates to a method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in the presence of visible light. With aza-metalloporphyrin containing sulfur as a visible light catalyst, 1,8-diazabicycloundecene-7-alkene as an auxiliary agent, and oxygen as an oxidant,asymmetric secondary amine is subjected to catalytic oxidation under irradiation of visible light of lambda being larger than or equal to 420nm, so as to obtain the oxidation product imine. A new andefficient imine production way is provided.

Synthesis of N-methyl imines in the presence of poly(N-vinylpyridine) as a reusable solid base catalyst by a mechanochemical process

The synthesis of N-methyl imines was performed in the presence of catalytic amounts of poly(4-vinylpyridine) in high yields and rapidly at room temperature by a ball milling process. This new method has some advantages including good yields for relatively unreactive carbonyl compounds and short reaction times as well as being green in terms of avoiding the use of toxic reagents and solvents. The major advantage of this process is that the catalyst can be easily regenerated and reused several times without any significant loss of activity.

Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction

A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogeni

Thiazolidinones derived from dynamic systemic resolution of complex reversible-reaction networks

A complex dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on kinetically controlled lipase-catalyzed transformations. This resulted in the formation of cyclized products, where two thiazolidinone compounds were efficiently produced from a range of potential transformations.

A latent reaction in a model GFP chromophore revealed upon confinement: Photohydroxylation of ortho -halo benzylidene-3-methylimidazolidiones via an electrocylization process

Excited state behavior of halogen substituted model GFP chromophores was investigated in an acetonitrile solution and in a confined environment provided by an octa acid capsule in water. Of the ortho, meta, and para halogen substituted GFP chromophores on

Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes

A one-pot solvent-free synthesis of N-methyl imines in good to excellent yields was performed by grinding together aromatic aldehydes and methylamine hydrochloride in the presence of a base. The best yields were achieved when an excess of methylamine hydrochloride and inexpensive sodium hydrogen carbonate was used (usually in a molar ratio ArCHO/CH3NH2· HCl/NaHCO3 = 1:5:5), allowing the reaction to proceed for 1 h (in the case of aromatic aldehydes containing electron-withdrawing substituents) or overnight (in the case of electron-rich aldehydes). After a simple work-up (extraction with diethyl ether) the obtained products were mostly pure enough for spectral characterization. In this way, 31 N-methyl imines were prepared, among which eight were synthesized for the first time. Their structures were elucidated by spectral means (1H- and 13C-NMR, IR, MS) whenever it was possible. In the case of salicylaldehyde and 4-chlorobenzaldehyde, the synthesis of the corresponding imines was also conducted on a gram-scale with a 72% and 84% isolated yield, respectively. The present approach not only provides good to high yields, but also eliminates the disadvantages of the traditional synthesis of N-methyl imines, such as the use of hazardous solvents and more or less expensive catalysts and the necessity of work/handling with an anhydrous gas in pressurized containers.

Steric and electronic effects in capsule-confined green fluorescent protein chromophores

The turn-on of emission in fluorescent protein chromophores sequestered in an "octaacid" capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett σ parameters. The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule.