Month: January 2023

Synthesis and in vitro evaluation of three novel radiotracers for imaging of metabotropic glutamate receptor subtype 2 in rat brain was written by Kumata, Katsushi;Yamasaki, Tomoteru;Hatori, Akiko;Zhang, Yiding;Mori, Wakana;Fujinaga, Masayuki;Xie, Lin;Okubo, Takayuki;Nengaki, Nobuki;Zhang, Ming-Rong. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Product Details of 58333-75-8 This article mentions the following:

The purpose of this study was to develop three new radiotracers, 1-(cyclopropylmethyl)-4-([¹¹C/¹⁸F]substituted-phenyl)piperidin-1-yl-2-oxo-1,2-dihydropyridine-3-carbonitrile I [R = 2-O¹¹CH₃ (II), 3-O¹¹CH₃ (III), 2-OCH₂CH₂¹⁸F (IV)], and to examine their specific bindings with metabotropic glutamate receptor subtype 2 (mGluR2) in rat brain sections by using in vitro autoradiog. These compounds were found to possess potent in vitro binding affinities (K_i: 8.0-34.1 nM) for mGluR2 in rat brain homogenate. II, III, and IV were synthesized by [¹¹C/¹⁸F]alkylation of the corresponding phenol precursors with [¹¹C]methyl iodide or [¹⁸F]fluoroethyl bromide with >98% radiochem. purity and 80-130 GBq/μmol specific activity at the end of synthesis. In vitro autoradiog. indicated that these radiotracers showed heterogeneous specific bindings in mGluR2-rich brain regions, such as the cerebral cortex, striatum, hippocampus, and granular layer of the cerebellum. In the experiment, the researchers used many compounds, for example, 4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8Product Details of 58333-75-8).

4-(2-Methoxyphenyl)piperidine (cas: 58333-75-8) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Product Details of 58333-75-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Syntheses in the piperidine series. I. A facile synthesis of 4-piperidinol and the preparation of related compounds was written by Bowden, K.;Green, P. N.. And the article was included in Journal of the Chemical Society in 1952.Recommanded Product: 4045-22-1 This article mentions the following:

(ClCH₂)₂CHOH (65 g.) and 54 g. NaCN in 60 ml. H₂O, warmed 40 min. at 50-5° and kept overnight, give 6.3 g. ClCH₂CH(OH)CH₂CN and 23.3 g. (NCCH₂)₂CHOH (I). I (45 g.) in 400 ml. EtOH, hydrogenated over 10 g. Raney Ni at 50°/50 atm. (2 hrs.), gives 17.6 g. 4-piperidinol (II), b₁₀ 110-15°; chloroplatinate, m. 195° (decomposition) [Koenigs and Neumann, C.A. 9, 2254, gave 184-7° (decomposition)]; II and dilute H₂SO₄ give the sulfate, m. 272-4° (K. and N. gave 263-6°); with 4 mols. H₂O, m. 66-8°. The EtOH-insoluble matter from II yields the dipicrate, yellow, m. 238° (decomposition), of (CH₂)₅(NH₂)₂. II (3 g.) in 10 g. 47% HBr, evaporated to dryness in vacuo, the residue in 10 ml. hot EtOH evaporated in vacuo, and the product refluxed 10 min. with 5 g. PBr₃, gives 2.8 g. 4-bromopiperidinium bromide (III), m. 192-3° (decomposition); picrate, yellow, m. 162-3°; sulfate, m. 163-4°. III (2.45 g.) in 15 ml. H₂O, added to 1.54 g. BzCl in 5 ml. C₆H₆, followed dropwise with 1.27 g. Na₂CO₃ in 12.7 ml. H₂O at 5°, gives 2 g. 1-benzoyl-4-bromopiperidine, m. 67-9°. II (5 g.) in 6 ml. AcOMe, refluxed 78 hrs., gives 3 g. 1-acetyl-4-piperidinol (IV), m. 66-7°; 2.5 g. II, 1.5 AcONH₂, and 5 g. cyclohexanol, refluxed 6 hrs., give 1.5 g. IV. (ClCH₂CH₂)₂CO (4.65 g.) in 30 ml. absolute EtOH, treated dropwise (45 min.) with 6.3 g. Na₂CO₃ in 70 ml. H₂O and simultaneously with MeNH₂, and refluxed 1 hr., give 0.75 g. 4-methylpiperidone, b₁₄ 55-9°. II (5 g.) in 8 g. 90% HCO₂H, treated with 5 g. 40% aqueous HCHO, heated 8 hrs. on the steam bath, treated the next day with 10 ml. concentrated HCl, and refluxed 5 min., gives 4.3 g. 1-methyl-4-piperidinol, b₁₀ 95-6° [methiodide, m. 327° (decomposition)]. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1Recommanded Product: 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Recommanded Product: 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines was written by Henry Blackwell, J.;Harris, Georgia R.;Smith, Milo A.;Gaunt, Matthew J.. And the article was included in Journal of the American Chemical Society.Category: piperidines This article mentions the following:

Here, authors report an operationally straightforward, multicomponent protocol for the synthesis of a range of functionally and structurally diverse α-trialkyl-α-tertiary amines, which makes use of three readily available components: dialkyl ketones, benzylamines, and alkenes. The strategy relies on the of use visible-light-mediated photocatalysis with readily available Ir(III) complexes to bring about single-electron reduction of an all-alkyl ketimine species to an α-amino radical intermediate; the α-amino radical undergoes Giese-type addition with a variety of alkenes to forge the α-trialkyl-α-tertiary amine center. The mechanism of this process is believed to proceed through an overall redox neutral pathway that involves photocatalytic redox-relay of the imine, generated from the starting amine-ketone condensation, through to an imine-derived product. This is possible because the presence of a benzylic amine component in the intermediate scaffold drives a 1,5-hydrogen atom transfer step after the Giese addition to form a stable benzylic α-amino radical, which is able to close the photocatalytic cycle. Authors believe this transformation will provide convenient access to previously unexplored α-trialkyl-α-tertiary amine scaffolds that should be of considerable interest to practitioners of synthetic and medicinal chem. in academic and industrial institutions. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Category: piperidines).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives.Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chiral amino-amides as solution phase and immobilized ligands for the catalytic asymmetric alkylation of aromatic aldehydes was written by Lesma, Giordano;Danieli, Bruno;Passarella, Daniele;Sacchetti, Alessandro;Silvani, Alessandra. And the article was included in Letters in Organic Chemistry in 2006.Formula: C12H15NO3S This article mentions the following:

Novel chiral amino-amide 9-keto-bispidines are investigated as ligands in the addition reaction of diethylzinc to aromatic aldehydes. The ligands are easily obtained by a single-step procedure starting from com. available products. Selected ligands were also supported onto different insoluble resins in order to test their activity as heterogeneous catalysts. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes was written by Law, James A.;Bartfield, Noah M.;Frederich, James H.. And the article was included in Angewandte Chemie, International Edition in 2021.Application In Synthesis of 1-Tosylpiperidin-4-one This article mentions the following:

Me groups are ubiquitous in biol. active mols. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp₂Ti(μ-Cl)(μ-CH₂)AlMe₂ (Tebbe’s reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcs., ethers, amides, carbamates, and basic amines. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Application In Synthesis of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Application In Synthesis of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hindered dialkyl ether synthesis with electrogenerated carbocations was written by Xiang, Jinbao;Shang, Ming;Kawamata, Yu;Lundberg, Helena;Reisberg, Solomon H.;Chen, Miao;Mykhailiuk, Pavel;Beutner, Gregory;Collins, Michael R.;Davies, Alyn;Del Bel, Matthew;Gallego, Gary M.;Spangler, Jillian E.;Starr, Jeremy;Yang, Shouliang;Blackmond, Donna G.;Baran, Phil S.. And the article was included in Nature (London, United Kingdom) in 2019.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate This article mentions the following:

Hindered ethers are of high value for various applications; however, they remain an underexplored area of chem. space because they are difficult to synthesize via conventional reactions. Such motifs are highly coveted in medicinal chem., because extensive substitution about the ether bond prevents unwanted metabolic processes that can lead to rapid degradation in vivo. Here we report a simple route towards the synthesis of hindered ethers, in which electrochem. oxidation is used to liberate high-energy carbocations from simple carboxylic acids. These reactive carbocation intermediates, which are generated with low electrochem. potentials, capture an alc. donor under non-acidic conditions; this enables the formation of a range of ethers (more than 80 have been prepared here) that would otherwise be difficult to access. The carbocations can also be intercepted by simple nucleophiles, leading to the formation of hindered alcs. and even alkyl fluorides. This method was evaluated for its ability to circumvent the synthetic bottlenecks encountered in the preparation of 12 chem. scaffolds, leading to higher yields of the required products, in addition to substantial reductions in the number of steps and the amount of labor required to prepare them. The use of mol. probes and the results of kinetic studies support the proposed mechanism and the role of additives under the conditions examined The reaction manifold that we report here demonstrates the power of electrochem. to access highly reactive intermediates under mild conditions and, in turn, the substantial improvements in efficiency that can be achieved with these otherwise-inaccessible intermediates. In the experiment, the researchers used many compounds, for example, Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate).

Benzyl 3-hydroxypiperidine-1-carboxylate (cas: 95798-22-4) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Quality Control of Benzyl 3-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Red-Light-Mediated Barton-McCombie Reaction was written by Ogura, Akihiro;Ichii, Naoki;Shibata, Kouhei;Takao, Ken-ichi. And the article was included in Bulletin of the Chemical Society of Japan in 2020.SDS of cas: 33439-27-9 This article mentions the following:

A red-light-mediated Barton-McCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis was written by Lackner, Gregory L.;Quasdorf, Kyle W.;Pratsch, Gerald;Overman, Larry E.. And the article was included in Journal of Organic Chemistry in 2015.Safety of 1-Boc-4-Hydroxy-4-methylpiperidine This article mentions the following:

The coupling of tertiary carbon radicals with alkene acceptors is an underdeveloped strategy for uniting complex carbon fragments and forming new quaternary carbons. The scope and limitations of a new approach for generating nucleophilic tertiary radicals from tertiary alcs. and utilizing these intermediates in fragment coupling reactions is described. In this method, the tertiary alc. is first acylated to give the tert-alkyl N-phthalimidoyl oxalate, which in the presence of visible-light, catalytic Ru(bpy)₃(PF₆)₂, and a reductant fragments to form the corresponding tertiary carbon radical. In addition to reductive coupling with alkenes, substitution reactions of tertiary radicals with allylic and vinylic halides is described. A mechanism for the generation of tertiary carbon radicals from tert-alkyl N-phthalimidoyl oxalates is proposed that is based on earlier pioneering investigations of Okada and Barton. Deuterium labeling and competition experiments reveal that the reductive radical coupling of tert-alkyl N-phthalimidoyl oxalates with electron-deficient alkenes is terminated by hydrogen-atom transfer. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Safety of 1-Boc-4-Hydroxy-4-methylpiperidine).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Safety of 1-Boc-4-Hydroxy-4-methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents was written by Habermann, Joerg;Ley, Steven V.;Scott, James S.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry in 1998.SDS of cas: 33439-27-9 This article mentions the following:

Polymer-supported reagents and other solid sequestering agents, e.g., polymer-supported (dimethylamino)pyridine and Amberlyst A21, were used to generate a library of piperidinothiomorpholines, e.g., I (R = 4-Me, 4-F, 3-F₃C; R¹ = 4-MeO, H, 3-F₃C, 3,4-Cl₂), without any chromatog. purification steps. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

A facile, environmentally benign sulfonamide synthesis in water was written by Deng, Xiaohu;Mani, Neelakandha S.. And the article was included in Green Chemistry in 2006.Product Details of 33439-27-9 This article mentions the following:

A facile, environmentally benign synthesis of sulfonamides under dynamic pH control in aqueous media is described. This methodol. uses equimolar amounts of amino compounds and arylsulfonyl chlorides and omits the use of organic bases. Isolation of products involves only filtration after acidification. Excellent yields and purity were obtained without further purification In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Product Details of 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Product Details of 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem