531-67-9

Usage

Uses

Used in Organic Synthesis:
2,2-BIPIPERIDINE is utilized as a building block in organic synthesis for its ability to form a variety of complex organic compounds. Its structural properties allow it to be a key component in the creation of new molecules with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,2-BIPIPERIDINE is used as a precursor for the synthesis of various pharmaceuticals. Its unique structure contributes to the development of new drugs, potentially leading to advancements in medicinal chemistry.
Used in Agrochemicals:
2,2-BIPIPERIDINE also serves as a precursor in the synthesis of agrochemicals, playing a role in the development of new pesticides or other agricultural chemicals that can improve crop protection and yield.
Used as a Chelating Agent:
2,2-BIPIPERIDINE has been investigated for its potential as a chelating agent for metal ions. This application is significant in various chemical processes where metal ion sequestration is necessary, such as in environmental remediation or in stabilizing certain chemical reactions.
Used as a Ligand in Coordination Chemistry:
Furthermore, 2,2-BIPIPERIDINE is recognized for its use as a ligand in coordination chemistry. Its ability to bind to metal centers is valuable for the construction of coordination compounds, which have applications in catalysis, materials science, and other areas of chemistry.

Upstream product

• 110-89-4 piperidine 
• 56528-77-9 (+/-)-2-cyclohexyl-piperidine 
• 110-82-7 cyclohexane 
• 366-18-7 [2,2]bipyridinyl 
• 110-86-1 pyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 536-74-3 phenylacetylene 

Downstream Products

• 366-18-7 [2,2]bipyridinyl 
• 18700-70-4 r-6H,c-11a,c-11b-6-p-nitrophenylperhydrodipyrido<1,2-c:2',1'-e>imidazole 
• 18700-70-4 r-6H,c-11a,t-11b-6-p-nitrophenylperhydrodipyrido<1,2-c:2',1'-e>imidazole 
• 18700-70-4 r-6H,t-11a,t-11b-6-p-nitrophenylperhydrodipyrido<1,2-c:2',1'-e>imidazole 

Relevant academic research and scientific papers

Optical Resolution of DL-2,2'-Bipiperidine through its Cobalt(III) Complex

The separation of racemic 2,2'-bipiperidine and the meso form has been performed through the dihydrochloride salt of the diamine.The reaction of racemic 2,2'-bipiperidine with 2)6>3- has been shown to yield only one DL pair of trans-bis(2,2'-bipiperidine)dinitrocobalt(III) complex ion.The dinitro-complex has been characterized and optically resolved using ammonium D-2-bromo-4,7-dimethyl-3-oxobicycloheptane-7-methanesulphonate.Optically pure (-)589-2,2'-bipiperidine was recovered from the less soluble diastereoisomer and shows a specific rotation of -12.2 deg.The stereoselective formation of the trans-dinitro-complex is discussed in relation to the predictions of strain energy minimization calculations.

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Cu ion-exchanged and Cu nanoparticles decorated mesoporous ZSM-5 catalysts for the activation and utilization of phenylacetylene in a sustainable chemical synthesis

Mesoporous ZSM-5 was synthesized using a 1,4-diazabicyclo[2.2.2]octane based multi-cationic surfactant as a structure directing agent. Cu2+ exchanged mesoporous ZSM-5 was prepared by the ion-exchange process. Cu nanoparticles decorated mesoporous ZSM-5 was prepared using NaBH4 as a reducing agent. Materials were characterized by the complementary combination of X-ray diffraction, N2-adsorption, UV-visible, and scanning/transmission electron microscopic techniques. For comparative purposes, Cu2+ exchanged ZSM-5, HY, and NaY; and Cu nanoparticles decorated conventional ZSM-5, SBA-15, and Al2O3 samples were also prepared. A sustainable catalytic process was developed for the selective synthesis of indolizine, chalcone, and triazole derivatives using a mesoporous ZSM-5 based heterogeneous catalyst. A multi-component synthetic strategy is reported here for the selective synthesis of the above mentioned chemicals that involves phenylacetylene as one of the building blocks. Control experiments were performed to ascertain the proposed reaction pathways. Recycling and leaching experiments were performed to demonstrate the sustainability and robustness of the catalytic process. Among these catalysts, Cu nanoparticles decorated mesoporous ZSM-5 exhibited the highest activity in all these reactions. The catalyst was found to be highly stable and it was possible to recycle the catalyst five times with no appreciable loss in the activity. A wide range of indolizine, chalcone, and 1,2,3-triazole derivatives were prepared in high yields using this catalyst.

Visible light induced green transformation of primary amines to imines using a silicate supported anatase photocatalyst

Catalytic oxidation of amine to imine is of intense present interest since imines are important intermediates for the synthesis of fine chemicals, pharmaceuticals, and agricultural chemicals. However, considerable efforts have been made to develop efficient methods for the oxidation of secondary amines to imines, while little attention has until recently been given to the oxidation of primary amines, presumably owing to the high reactivity of generated imines of primary amines that are easily dehydrogenated to nitriles. Herein, we report the oxidative coupling of a series of primary benzylic amines into corresponding imines with dioxygen as the benign oxidant over composite catalysts of TiO2 (anatase)-silicate under visible light irradiation of λ > 460 nm. Visible light response of this system is believed to be as a result of high population of defects and contacts between silicate and anatase crystals in the composite and the strong interaction between benzylic amine and the catalyst. It is found that tuning the intensity and wavelength of the light irradiation and the reaction temperature can remarkably enhance the reaction activity. Water can also act as a green medium for the reaction with an excellent selectivity. This report contributes to the use of readily synthesized, environmentally benign, TiO2 based composite photocatalyst and solar energy to realize the transformation of primary amines to imine compounds.

Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides

On the basis of the mechanistic insight that more than one Lewis basic moiety (phosphoramide) is involved in the rate- and stereochemistry-determining step of enantioselective allylation, bidentate chiral phosphoramides were developed. Different chiral phosphoramide moieties were connected by tethers of methylene chains of varying length. The rate and enantioselectivity of allylation with allyltrichlorosilane promoted by the bidentate phosphoramides was found to be highly dependent on the tether length. A new phosphoramide based on a 2,2′-bispyrrolidine skeleton has been designed and afforded good yield, efficient turnover, and high enantioselectivity in allylation reactions. The synthesis of enantiopure 2,2′-bispyrrolidine was easily accomplished on large scale by photodimerization of pyrrolidine followed by resolution with L(or D)-tartaric acid. The scope of the allylation reaction was examined with variously substituted allylic trichlorosilanes and unsaturated aldehydes. This method has been applied to the construction of stereogenic, quaternary centers by the addition of unsymmetrically γ-disubstituted allylic trichlorosilanes.

Functionalization of nitrogen and oxygen containing heterocycles by mercury photosensitized dehydrodimerizations

Nitrogen and oxygen containing heterocycles can be functionalized by mercury photosensitization.

Facile Reduction of Pyridines with Nickel-Aluminum Alloy

Nickel-aluminum alloy in dilute base can be used to reduce a variety of pyridines, quinolines, and isoquinoline to the corresponding piperidines, 1,2,3,4-tetrahydroquinolines, and 1,2,3,4-tetrahydroisoquinoline in good yield.The reaction is simple to perform, and high temperatures, high pressures, or hydrogen atmospheres are not required.The reaction is accelerated by substituents in the 2-position and by electron-withdrawing groups in the 3- and 4-positions while electron-supplying groups in the 3- and 4-positions retard the reaction.The major product isolated from the reduction of 2-phenylpyridine was 2-cyclohexylpiperidine hydrochloride.With isoniazid (1) and iproniazid (4) the pyridine ring is hydrogenated before the hydrazine is cleaved.