4096-21-3

Usage

Uses

Used in Agrochemical Industry:
1-Phenylpyrrolidine is used as a key intermediate for the synthesis of agrochemicals, specifically for the development of compounds that target and control intestinal coccidiosis in livestock. Its role in this industry is crucial for creating effective treatments to protect animals from parasitic infections.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1-Phenylpyrrolidine serves as an essential intermediate in the production of various drugs. Its unique structure allows for the creation of molecules with specific therapeutic properties, contributing to the development of new medications.
Used in Dye Industry:
1-Phenylpyrrolidine is also utilized in the dyestuff field, where it acts as an intermediate for synthesizing a range of dyes with different color properties. Its presence in this industry is vital for the production of dyes with specific characteristics, catering to various applications and requirements.

Synthesis Reference(s)

Tetrahedron, 42, p. 259, 1986 DOI: 10.1016/S0040-4020(01)87426-3Tetrahedron Letters, 31, p. 2991, 1990 DOI: 10.1016/S0040-4039(00)89006-1

InChI:InChI=1/C10H13N/c1-2-6-10(7-3-1)11-8-4-5-9-11/h1-3,6-7H,4-5,8-9H2

Upstream product

• 109-99-9 tetrahydrofuran 
• 62-53-3 aniline 
• 635-90-5 1-phenylpyrrole 
• 83-25-0 N-phenylmaleimide 
• 6517-80-2 4-(phenylamino)butan-1-ol 
• 110-52-1 1,4-dibromo-butane 
• 110-63-4 Butane-1,4-diol 
• 110-56-5 1,4-dichlorobutane 
• 42330-98-3 N-4-Chlorbutylanilin 
• 121-69-7 N,N-dimethyl-aniline 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 874-52-2 N,N-dimethylaniline N-oxide 
• 594-19-4 tert.-butyl lithium 
• 5430-83-1 N-phenyl-succinamic acid methyl ester 

Downstream Products

• 89787-48-4 2-[2-(4-Pyrrolidin-1-yl-phenylazo)-benzothiazol-6-yloxy]-ethanol 
• 89505-26-0 5-Nitro-2-(4-pyrrolidin-1-yl-phenylazo)-benzonitrile 
• 89505-22-6 (4-Pyrrolidin-1-yl-phenyl)-(4-trifluoromethyl-phenyl)-diazene 
• 128451-05-8 1-pyrrolidino-α-(perfluoroheptyl)-β,β-dicyanostyrene 
• 106365-87-1 1-(4-Thiocyanophenyl)pyrrolidine 
• 95245-65-1 3-nitro-4',4''-dipyrrolidinotriphenylmethane 
• 87872-24-0 4,4'-dipyrrolidinotriphenylmethane 
• 40637-76-1 (4-Pyrrolidin-1-yl-phenyl)-p-tolyl-diazene 
• 40637-77-2 (4-Chloro-phenyl)-(4-pyrrolidin-1-yl-phenyl)-diazene 
• 89505-23-7 1-[4-(4-Pyrrolidin-1-yl-phenylazo)-phenyl]-ethanone 
• 89505-20-4 (4-Methoxy-phenyl)-(4-pyrrolidin-1-yl-phenyl)-diazene 
• 64193-73-3 (4-Nitro-phenyl)-(4-pyrrolidin-1-yl-phenyl)-diazene 
• 10282-34-5 Phenyl-(4-pyrrolidin-1-yl-phenyl)-diazene 
• 89505-21-5 (4-Bromo-phenyl)-(4-pyrrolidin-1-yl-phenyl)-diazene 

Relevant academic research and scientific papers

Metal-free protocol for the synthesis of N-arylpyrrolidines catalyzed by hydrogen iodine

A metal-free and efficient approach to N-arylpyrrolidines from arylamines and cyclic ethers catalyzed by hydrogen iodine is described. In this protocol, no additive is added and a wide range of N-arylpyrrolidines are synthesized with up to 99% yield. Reaction mechanism involving iodine radical is proposed.

Dual Photoredox/Cobaloxime Catalysis for Cross-Dehydrogenative α-Heteroarylation of Amines

We report a dual-catalytic platform for the cross-dehydrogenative-coupling between (benzo-)thiazoles and amines which combines low loadings of an iridium photoredox catalyst and a cobaloxime catalyst under blue light irradiation. This transformation occurs without stoichiometric oxidants, giving products in moderate to excellent yields. DFT calculations support the key role of Co(II) for rearomatization of the radical-addition intermediate to generate the product.

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.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

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

NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media

The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is

Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides

Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Half-sandwich (η5-Cp?)Rh(iii) complexes of pyrazolated organo-sulfur/selenium/tellurium ligands: Efficient catalysts for base/solvent free C-N coupling of chloroarenes under aerobic conditions

Three new pyrazolated chalcogenoether ligated Rh(iii) half-sandwich complexes (1-3) were synthesised by the thermal reaction of chalcogenoether (S, Se and Te) substituted 1H-pyrazole ligands (L1-L3) and [(η5-C5Me5)RhCl]2 in methanol. The complexes were fully characterised by various spectroscopic techniques, and the molecular structures of complexes 1 and2 were also established through single crystal X-ray crystallographic analysis, which indicates a pseudo-octahedral half-sandwich piano-stool geometry around the rhodium metal. All three complexes were found to be thermally stable and insensitive towards air and moisture. One mol% of Rh(iii) complexes (1-3) along with 10 mol% of Cu(OAc)2 were explored for the Buchwald-Hartwig type C-N coupling reactions of amine and aryl chloride. Good to excellent yields (89-92%) of the coupling products were obtained with seleno- and thio-ether functionalised pyrazolated Rh(iii) complexes (1 and 2), while an average yield (39%) was obtained with the telluro-ether functionalised complex (3). In contrast to the previously reported C-N coupling reactions the present reaction works under solvent- and base-free conditions, and the coupling reaction is accomplished in just 6 h with a high yield of the coupling product. The present methodology was also found to be efficient for a wide variety of functionalised aryl halides, and aliphatic or aromatic amines (1° and 2°). Moreover, the reaction also enables the C-N coupling of electron-withdrawing substrates and base-sensitive functionalities.