156-41-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Chlorophenethylamine is used as a reactant for the preparation of isoalloxazine derivatives, which are known as cholinesterase inhibitors. These derivatives have potential therapeutic applications in the treatment of Alzheimer's disease, as they can help improve cognitive function by inhibiting the breakdown of acetylcholine, a neurotransmitter that plays a crucial role in memory and learning.
Used in Alzheimer Therapy:
As a key component in the synthesis of isoalloxazine derivatives, 4-Chlorophenethylamine contributes to the development of drugs that can potentially alleviate the symptoms of Alzheimer's disease. By acting as cholinesterase inhibitors, these drugs can enhance the levels of acetylcholine in the brain, thereby improving cognitive function and slowing down the progression of the disease.

InChI:InChI=1/C8H10ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2/p+1

Upstream product

• 13312-83-9 4-chloromandelonitrile 
• 99839-78-8 3-(4-chlorophenyl)propionic amide 
• 52085-96-8 3-(4-chlorophenyl)propanoyl chloride 
• 140-53-4 p-chlorobenzyl cyanide 
• 2742-77-0 Bis-(β-nitroso-4-chlor-styrol) 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 7424-00-2 DL-Phe(4Cl) 
• 128915-11-7 N-[2-(4-Chloro-phenyl)-ethyl]-N'-(4-nitro-phenyl)-formamidine 
• 197785-44-7 1-(1-azido-2-bromoethyl)-4-chlorobenzene 
• 497-25-6 dimethylenecyclourethane 
• 108-90-7 chlorobenzene 
• 7647-01-0 hydrogenchloride 
• 64-04-0 phenethylamine 
• 60947-43-5 1-chloro-4-(2-nitroethyl)benzene 

Downstream Products

• 100716-33-4 isonicotinic acid-(4-chloro-phenethylamide) 
• 108541-57-7 N-(4-chloro-phenethyl)-β-alanine nitrile 
• 92328-94-4 (4-chloro-phenethylamino)-acetaldehyde diethylacetal 
• 26328-69-8 3-(4-chloro-phenethyl)-5-cyclohexyl-[1,3,5]thiadiazinane-2-thione 
• 26369-79-9 5-(4-chloro-phenethyl)-3-(2-hydroxy-ethyl)-[1,3,5]thiadiazinane-2-thione 
• 5842-73-9 3-(4-chloro-phenethyl)-5-(2-hydroxy-ethyl)-[1,3,5]thiadiazinane-2-thione 
• 5842-75-1 3-(4-chloro-phenethyl)-5-hexyl-[1,3,5]thiadiazinane-2-thione 
• 26366-96-1 3-(4-chloro-phenethyl)-5-(1,1,3,3-tetramethyl-butyl)-[1,3,5]thiadiazinane-2-thione 
• 26367-07-7 3,5-bis-(4-chloro-phenethyl)-[1,3,5]thiadiazinane-2-thione 
• 56224-52-3 N,N'-Bis-[2-(4-chloro-phenyl)-ethyl]-4,6-dinitro-benzene-1,3-diamine 
• 6121-08-0 1-<4-Chlor-phenaethyl>-biuret 
• 6121-07-9 1,1-Diaethyl-5-<4-chlor-phenaethyl>-biuret 
• 28646-29-9 N²-<4-Chlor-phenaethyl>-N-phenaethyl-β-DL-asparagin 
• 46234-79-1 p-Chlorophenethylguanidine 

Relevant academic research and scientific papers

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

Method for preparing lorcaserin

The invention discloses a method for preparing lorcaserin. Specifically, the method comprises the steps: taking p-chlorophenylacetonitrile as an initial raw material, preparing p-chlorophenylethylamine through reduction; carrying out a reaction with p-toluenesulfonyl chloride to form an amino occupying intermediate; enabling the intermediate to carry out a reaction with monochloroacetone under analkaline condition to form N-(2-(4-chlorphenyl)ethyl)-4-methyl-N-(2-propionyl)benzenesulfonamide, and then carrying out reduction, chlorination, p-toluenesulfonyl removal and intramolecular Friedel-Crafts alkylation to synthesize 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzoazepine, carrying out L-(+)-tartaric acid resolution and alkalization on azepine to remove tartaric acid, and acting with hydrogen chloride diethyl ether to salify to prepare lorcaserin. The method has the characteristics of simple synthesis method, good reaction selectivity, high product purity, environmental protectionand low preparation cost.

Enantioselective Sequential-Flow Synthesis of Baclofen Precursor via Asymmetric 1,4-Addition and Chemoselective Hydrogenation on Platinum/Carbon/Calcium Phosphate Composites

Continuous-flow synthesis of baclofen precursor (2) was achieved using achiral and chiral heterogeneous catalysts in high yield with high enantioselectivity. The key steps are chiral calcium-catalyzed asymmetric 1,4-addition of a malonate to a nitroalkene and chemoselective reduction of a nitro compound to the corresponding amino compound by using molecular hydrogen. A dimethylpolysilane (DMPS)-modified platinum catalyst supported on activated carbon (AC) and calcium phosphate (CP) has been developed that has remarkable activity for the selective hydrogenation of nitro compounds.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Old Concepts, New Application – Additive-Free Hydrogenation of Nitriles Catalyzed by an Air Stable Alkyl Mn(I) Complex

An efficient additive-free manganese-catalyzed hydrogenation of nitriles to primary amines with molecular hydrogen is described. The pre-catalyst, a well-defined bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dpre)(CO)3(CH3)] (dpre=1,2-bis(di-n-propylphosphino)ethane), undergoes CO migratory insertion into the manganese-alkyl bond to form acyl complexes which upon hydrogenolysis yields the active coordinatively unsaturated Mn(I) hydride catalyst [Mn(dpre)(CO)2(H)]. A range of aromatic and aliphatic nitriles were efficiently and selectively converted into primary amines in good to excellent yields. The hydrogenation of nitriles proceeds at 100 °C with a catalyst loading of 2 mol % and a hydrogen pressure of 50 bar. Mechanistic insights are provided by means of DFT calculations. (Figure presented.).

Method for synthesizing lorcaserin intermediate p-chlorophenethylamine

The invention discloses a method for synthesizing a lorcaserin intermediate, namely p-chlorophenethylamine. The method is characterized in that p-chlorophenethylamine is prepared from p-halogen chlorobenzene and halogenated ethylamine under the action of a catalyst, and the reaction process comprises the following steps: 1) uniformly mixing halogenated ethylamine, a protecting agent, an alkali 1 and a solvent S1, stirring at 50-70 DEG C to perform a reaction for 6-8h, and filtering off solids so as to obtain a mixture M1; 2) under the protection of a protection gas, uniformly mixing p-halogenchlorobenzene, copper iodide, a solid alkali and a solvent S2, controlling a reaction temperature to 130-145 DEG C and reaction pressure to 3-5atm, stirring for 50-70min, dropping the mixture M1, controlling the reaction temperature to 150-170 DEG C and the reaction pressure to 5-7atm after dropping is completed, and carrying out a reaction for 1-2 so as to obtain a mixture M2; 3) putting a hydrochloric acid solution into the mixture M2, controlling the reaction temperature to 80-90 DEG C and t he reaction pressure to 2-3atm, and carrying out a reaction for 40-60min so as to obtain a mixture M3; and 4) putting an alkali 2 into the mixture M3 to adjust the pH value to 4, controlling the temperature to be less than 70 DEG C, cooling, leaving to stand and layer, washing an organic phase withwater, drying with a drying agent, and concentrating and evaporating off the solvents, thereby obtaining a product. The method is simple in operation, and no toxic substance is used.

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams

Ru(bpy)3]2+-cored supramolecular organic framework SMOF-1, assembled from a [Ru(bpy)3]2+-derived hexaarmed molecule and cucurbit[8]uril, has been demonstrated to heterogeneously catalyze visible light-induced reduction of phenyl, benzyl, 2-phenylethyl and 3-phenylpropyl azides in acetonitrile to produce the corresponding amines in good to high yields. For the last two kinds of azides that bear a CO2Me group at the para-position of the benzene ring, cascade reactions take place to generate the corresponding lactams in high yields. Compared with homogeneous control [Ru(bpy)3]Cl2, SMOF-1 exhibits remarkably increased photocatalysis activity as a result of synergistic effect of the [Ru(bpy)3]2+ units that form cubic cages to host the azide molecules and related intermediates. Moreover, SMOF-1 displays high recyclability and considerable photocatalysis activity after 3 to 12 runs.

Preparation method of lorcaserin intermediate

The invention discloses a preparation method of a lorcaserin intermediate (I). According to the preparation method, p-chlorobenzyl cyanide is taken as the primary raw material, and the lorcaserin intermediate (I) is obtained after reduction reactions and condensation reactions. The primary raw materials (p-chlorobenzyl cyanide and 1-chloro-2-propanol) are cheap and easily available; raw materials, which can easily get polluted and are explosive, such as sulfoxide chloride, hydrobromic acid, borane, and the like are not used; the preparation method will not produce a large amount of wastewater and is beneficial for the environment protection; moreover, the requirements on the protection of workers are lowered, and safe production is guaranteed. The route design is novel, the raw materials are easily available, the operation is simple and feasible, and the preparation method is environment-friendly and can be applied to massive industrial production.