88154-24-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Chlorophenyl)pyrrolidine is used as a building block for the synthesis of various pharmaceuticals, particularly those targeting the central nervous system. Its specific properties and reactivity contribute to the development of biologically active compounds, making it an essential precursor in drug discovery and synthesis.
Used in Medicinal Chemistry Research:
1-(3-Chlorophenyl)pyrrolidine is used as a key component in the research and development of new drugs, especially those with potential therapeutic applications. Its role in the synthesis of biologically active compounds aids in the advancement of medicinal chemistry and the creation of novel pharmaceuticals.
Used in Chemical Production:
1-(3-Chlorophenyl)pyrrolidine is used as a versatile intermediate in the production of other chemicals, such as pesticides and herbicides. Its ability to participate in various chemical reactions allows for its use in the synthesis of a wide range of chemical products, showcasing its utility beyond the pharmaceutical industry.

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 108-42-9 3-chloro-aniline 
• 110-52-1 1,4-dibromo-butane 
• 110-63-4 Butane-1,4-diol 
• 109-99-9 tetrahydrofuran 
• 15258-44-3 N-ethyl-3-chloroaniline 
• 123-75-1 pyrrolidine 
• 541-73-1 1,3-Dichlorobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 55-98-1 busulfan 

Relevant academic research and scientific papers

Preparation method for series synthesis of phenylpyrrolidine derivative under metal catalysis

The invention relates to a preparation method for series synthesis of a phenylpyrrolidine derivative under metal catalysis. The structural formula of the prepared phenylpyrrolidine derivative is shownin the figure 1. The preparation method comprises the following steps: preparing an N, N-diallyl aniline compound, a Grubbs catalyst, reduced iron powder and a reaction solvent, setting the reactiontemperature to be 40 DEG C, and fully stirring and reacting for 8-10 hours in a hydrogen atmosphere; and quenching after the reaction is monitored by TLC, extracting by using an organic solvent, drying, filtering, concentrating, and purifying by column chromatography to obtain the phenylpyrrolidine derivative with the yield of 62-81%. According to the method, the phenylpyrrolidine derivative is synthesized through one-pot series connection, raw materials are easy to obtain, operation is easy, repeatability is good, reaction conditions are mild, and the method is suitable for industrial production.

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.

Visible Light-Mediated (Hetero)aryl Amination Using Ni(II) Salts and Photoredox Catalysis in Flow: A Synthesis of Tetracaine

We report a visible light-mediated flow process for C-N cross-coupling of (hetero)aryl halides with a variety of amine coupling partners through the use of a photoredox/nickel dual catalyst system. Compared to the method in batch, this flow process enables a broader substrate scope, including less-activated (hetero)aryl bromides and electron-deficient (hetero)aryl chlorides, and significantly reduced reaction times (10 to 100 min). Furthermore, scale up of the reaction, demonstrated through the synthesis of tetracaine, is easily achieved, delivering the C-N cross-coupled products in consistently high yield of 84% on up to a 10 mmol scale.

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

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.

Phosphoryl chloride-mediated solvent-free synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers

A solvent- and metal-free protocol for preparation of N-aryl substituted azacycles from arylamines and cyclic ethers is described. In this method, the combination of POCl3 and DBU is crucial for conversion of arylamines and cyclic ethers to five- and six-membered azacycles. Without solvent, a variety of N-aryl-substituted, five-membered azacycles (pyrrolidines, 2-methylpyrrolidines, and piperidine) and six-membered azacycles (isoindolines and tetrahydroisoquinolines) are synthesized in high yields. This green method provides a sustainable and efficient approach for the preparation of azacycles from various cyclic ethers.

Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3

A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.

Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.

Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers

Titanium tetrachloride-mediated transformation of five- and six-membered cyclic ethers to the corresponding N-aryl-substituted azacycles is conducted in moderate to good yields under mild reaction conditions. Computational studies suggested a mechanism involving a Lewis acid-assisted ring-opening, a seven-membered metallacycle intermediate and a ring-closing process facilitated by direct participation of the metal center.

Synthetic method for five-component and six-component N-substituted nitrogenous heterocyclic compounds

The invention provides a synthetic method for preparing five-component and six-component N-substituted nitrogenous heterocyclic compounds from aromatic amine and five-component and six-component oxygen heterocyclic compounds via mediation by an aminotitanium intermediate. The five-component and six-component N-substituted nitrogenous heterocyclic compounds provided by the invention specifically refer to N-aryltetrahydropyrrole, N-aryl-2-methyltetrahydropyrrole, N-aryltetrahydropyrane, N-aryl-3,4-dihydro-1H-2-pyrane with a general chemical formula as defined in the specification. In the formula, Ar is a phenyl group, a 4-methylphenyl group, a 2-halophenyl group, a 3-halophenyl group or a 4-halophenyl group. The invention discloses the chemical structures and synthetic method of the compounds.