4280-30-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-chloro-phenyl)-pyrrolidine is used as a building block for the synthesis of various drugs, including varenicline, an FDA-approved medication for smoking cessation.
Used in Agrochemical Industry:
1-(4-chloro-phenyl)-pyrrolidine is used as a building block for the synthesis of various agrochemicals.
Used in Neurological and Psychiatric Disorders Treatment:
1-(4-chloro-phenyl)-pyrrolidine is used as a potential intermediate in the treatment of various neurological and psychiatric disorders, due to its ability to interact with certain receptors in the brain.

InChI:InChI=1/C10H12ClN/c11-9-3-5-10(6-4-9)12-7-1-2-8-12/h3-6H,1-2,7-8H2

Upstream product

• 106-47-8 4-chloro-aniline 
• 110-56-5 1,4-dichlorobutane 
• 123-75-1 pyrrolidine 
• 106-39-8 bromochlorobenzene 
• 109-99-9 tetrahydrofuran 
• 13519-75-0 N-ethyl-4-chloro-aniline 
• 106-46-7 para-dichlorobenzene 
• 55-98-1 busulfan 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 637-87-6 1-Chloro-4-iodobenzene 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 110-52-1 1,4-dibromo-butane 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 638-37-9 butanedial 

Downstream Products

• 41173-36-8 5-chloro-2-(1-pyrrolidinyl)nitrobenzene 

Relevant academic research and scientific papers

GAS-PHASE BASICITY AND IONIZATION ENERGIES IN SOME N-ARYLAZACYCLOALKANES

Proton-transfer equilibrium constant and ionization energy measurement were performed in the gas phase for a series of N-arylazacycloalkanes.The techniques used were Fourier transform ion cyclotron resonance (FT-ICR) and UV photoelectron spectroscopy (UPS

Direct Near Infrared Light–Activatable Phthalocyanine Catalysts

The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa

I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of: N -aryl-substituted azacycles

We have developed a protocol for efficient synthesis of N-aryl-substituted azacycles from aryl amines and cyclic ethers using I2/NaH2PO2 as the mediator. A diverse range of aryl amines and cyclic ethers undergo amination reaction to generate products in good to excellent yields with good functional group tolerance. This reaction can be easily scaled up to give N-aryl-substituted azacycles on a gram scale. Further chemical manipulation of the products enabled useful transformations of the quinoline ring, including bromination and acetylation. This journal is

Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis

Herein, we report a photoinduced dehydrogenation/(3+2) cycloaddition reaction by merging organic photoredox and Lewis acid catalysis, providing a straightforward and efficient approach for directly installing a benzofuran skeleton on the saturated aza-heterocycles. In this protocol, we also describe a novel organic photocatalyst (t-Bu-DCQ) with the advantages of a wider redox potential, easy synthesis, and a low price. Furthermore, the stepwise activation mechanism of dual C(sp3)-H bonds was demonstrated by a series of experimental and computational studies.

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU

A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.

N-heterocyclic carbene-Pd(II)-2-methyl-4,5-dihydrooxazole complex-catalyzed highly chemoselective mono-amination of dichlorobenzenes

The palladium-catalyzed chemoselective mono-amination of dichlorobenzenes was reported in this paper. Under the suitable conditions, all reactions involving the three isomers of dichlorobenzenes with various secondary and primary amines in the presence of

Tropane alkaloid compounds and method of manufacturing using sequential oxidation reactions

The present invention relates to a tropane alkaloid compound sequentially using an oxidative Mannich ring reaction and a method for producing the same. The present invention provides a tropane alkaloid compound having a structure of chemical formula 1 in

Organocatalytic Cascade β-Functionalization/Aromatization of Pyrrolidines via Double Hydride Transfer

An unprecedented cascade β-functionalization/aromatization reaction of N-arylpyrrolidines was established. A series of β-substituted arylpyrroles embedded with trifluoromethyl groups are provided directly from N-arylpyrrolidines. The deuterium-labeling experiments indicate that sequential double hydride transfer processes serve as the key steps in this transformation.

Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy

Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.