Category: piperidines

In 2019,Nature (London, United Kingdom) included an article 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.. Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate. The article was titled 《Hindered dialkyl ether synthesis with electrogenerated carbocations》. The information in the text is summarized as follows:

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 tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas: 109384-19-2Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate)

tert-Butyl 4-hydroxypiperidine-1-carboxylate(cas:109384-19-2) is a 4-hydroxypyridine with a boc protecting group used in the preparation of neurologically active agents and other pharmaceutical compounds.Reference of tert-Butyl 4-hydroxypiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 2012,Bollinger, Markus; Manzenrieder, Florian; Kolb, Roman; Bochen, Alexander; Neubauer, Stefanie; Marinelli, Luciana; Limongelli, Vittorio; Novellino, Ettore; Moessmer, Georg; Pell, Reinhard; Lindner, Wolfgang; Fanous, Joseph; Hoffman, Amnon; Kessler, Horst published 《Tailoring of Integrin Ligands: Probing the Charge Capability of the Metal Ion-Dependent Adhesion Site》.Journal of Medicinal Chemistry published the findings.Recommanded Product: 2-(Piperidin-4-yl)ethanol The information in the text is summarized as follows:

Intervention in integrin-mediated cell adhesion and integrin signaling pathways is an ongoing area of research in medicinal chem. and drug development. One key element in integrin-ligand interaction is the coordination of the bivalent cation at the metal ion-dependent adhesion site (MIDAS) by a carboxylic acid function, a consistent feature of all integrin ligands. With the exception of the recently discovered hydroxamic acids, all bioisosteric attempts to replace the carboxylic acid of integrin ligands failed. We report that phosphinates as well as monomethyl phosphonates represent excellent isosters, when introduced into integrin antagonists for the platelet integrin αIIbβ3. The novel inhibitors exhibit in vitro and ex vivo activities in the low nanomolar range. Steric and charge requirements of the MIDAS region were unraveled, thus paving the way for an in silico prediction of ligand activity and in turn the rational design of the next generation of integrin antagonists. In the experiment, the researchers used 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Recommanded Product: 2-(Piperidin-4-yl)ethanol)

2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Recommanded Product: 2-(Piperidin-4-yl)ethanol

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wang, Yi; Ji, Qingjie; Xu, Jixiang; Wan, Jun; Wang, Lei published their research in Separation and Purification Technology on December 1 ,2021. The article was titled 《Activation of peroxydisulfate using N-doped carbon-encapsulated Ni species for efficient degradation of tetracycline》.Quality Control of Triacetonamine The article contains the following contents:

In this study, N-doped porous carbon materials embedded with NiNx species (Ni@NC) were fabricated via the pyrolysis of Ni-doped zeolitic imidazolate frameworks-8 (ZIF-8) at the temperature of 900°C. The obtained Ni@NC-1 catalyst exhibited excellent activity in activating the peroxydisulfate (PDS) that was used for removing tetracycline (TC). The catalytic system exhibited good stability, wide pH adaptation, and high resistance to the operational environment. It was supposed that NiNx species could attach to PDS and act as electron acceptors to receive the electrons for activating the PDS, thus generating highly reactive superoxide radicals (·O-2) and singlet oxygen (1O2) species for rapid degradation of TC. The electron transfer and dissolved oxygen-derived ·O-2 were also responsible for the degradation of TC. In addition, the Ni@NC-1/PDS system exhibited high efficiency for removing oxytetracycline, ciprofloxacin, or levofloxacin. The results of this study would promote the design of other MOFs-derived carbon-encapsulated metal species for efficiently activating persulfate to remove antibiotics from the wastewater. In the experiment, the researchers used Triacetonamine(cas: 826-36-8Quality Control of Triacetonamine)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Quality Control of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《Synthesis of 3-(5-bromo-2,3-dimethoxy-phenyl)-[1, 2, 4] oxadiazole analogues and their evaluation as anti-Parkinson’s agents》 were Tiwari, Shashi B.; Kohli, D. V.. And the article was published in Medicinal Chemistry Research in 2008. Recommanded Product: 1690-72-8 The author mentioned the following in the article:

A series of 3-(5-bromo-2,3-dimethoxy-phenyl)-[1, 2, 4] oxadiazole derivatives, e.g., I, was prepared and their evaluation for anti-Parkinson’s activity was measured in vivo using albino rats. The result of the biol. activity studies indicated that some of the synthesized compounds have good agonistic activity on the dopamine receptors and a few of them were also found to be free from neurotoxicity. Thus these compounds might be useful ligands for studying the functional role of dopamine receptors in vivo. The high log P value of the compounds indicates that they should easily cross the blood-brain barrier (log P > 2.6). In the experimental materials used by the author, we found Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8Recommanded Product: 1690-72-8)

Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Recommanded Product: 1690-72-8

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The author of 《4-Substituted piperidines. III. Reduction of 1-benzyl-4-cyano-4-tert-aminopiperidines with lithium aluminum hydride》 were Hermans, Bert; van Daele, Paul; van de Westeringh, Cornelis; van der Eycken, Cyriel; Boey, Jozef; Janssen, Paul A. J.. And the article was published in Journal of Medicinal Chemistry in 1966. Safety of 4-Amino-1-benzylpiperidine-4-carbonitrile The author mentioned the following in the article:

cf. CA 63, 16298f. The reduction of 1-benzyl-4-cyano-4-tert-aminopiperidines with LiAlH4 is described; this reduction results in dentrilation, whereas the same reduction of the corresponding primary carboxamides yields the expected primary amines, which can easily be acylated. The obtained compounds are debenzylated, after which other substituents are introduced. These new compounds are virtually devoid of hypotensive or central nervous system depressant activity. In the part of experimental materials, we found many familiar compounds, such as 4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5Safety of 4-Amino-1-benzylpiperidine-4-carbonitrile)

4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Safety of 4-Amino-1-benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Samnick, Samuel; Brandau, Wolfgang; Sciuk, Joachim; Steinstraesser, Axel; Schober, Otmar published an article in Nuclear Medicine and Biology. The title of the article was 《Synthesis, characterization and biodistribution of neutral and lipid-soluble 99mTc-bisaminoethanethiol spiperone derivatives: possible ligands for receptor imaging with SPECT》.Formula: C13H17N3 The author mentioned the following in the article:

Using parts of the mol. structure of spiperone, two new ligand systems for complexation with 99mTc were prepared to develop potential receptor imaging agents for SPECT. The bis-aminoethanethiols (BAT): 1-benzyl-4-(2-mercapto-2-methyl-4-aza-pentyl)-4-(2-mercapto-2-methyl-propylamino)-piperidine (benzylpiperidyl-BAT, BP-BAT) and 1-[3-(4-fluorobenzoyl)-propyl]-4-(2-mercapto-2-methyl-4-aza-pentyl)-4-(2-mercapto-2-methyl-propylamino)-piperidine (butyrophenoylpiperidyl-BAT, BUP-BAT) form stable, neutral and lipid soluble complexes with 99mTc at pH ≥11 using SnCl2 as reducing agent in nearly quant. radiochem. yields. The biodistribution of 99mTc-BP-BAT and 99mTc-BUP-BAT in rats showed a moderate clearance from blood and low uptake and retention in the liver, whereas brain showed moderate uptake with prolonged retention. On the other hand, significant accumulations and retentions were observed in heart, kidney and lung with increasing oxygen/blood ratios up to 24 h. Within 24 h p.i. 22 and 29% of the injected dose (i.d.) of 99mTc-BP-BAT and 99mTc-BUP-BAT were eliminated by hepatobiliary excretion whereas 22% i.d. of both 99mTc-BAT complexes were excreted into the urine. Although first biodistribution studies of 99mTc-BP-BAT and 99mTc-BUP-BAT in rats showed relatively low brain uptake, the high uptake in peripheral, receptor rich organs indicates that compounds of this type may be used as a basis for further structural modification to develop agents with optimal properties for cerebral or peripheral receptor imaging with SPECT. In the experiment, the researchers used many compounds, for example, 4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5Formula: C13H17N3)

4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Formula: C13H17N3

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liang, Dongmin; Hu, Yongyou; Xiao, Chun; Wang, Guobin; Xie, Jieyun; Zhu, Xiaoqiang published their research in Science of the Total Environment on August 15 ,2022. The article was titled 《Highly efficient catalytic ozonation for ammonium in water upon γ-Al2O3@Fe/Mg with acidic-basic sites and oxygen vacancies》.Electric Literature of C9H17NO The article contains the following contents:

Catalytic ozonation has prospects in the advanced treatment of nitrogen removal, and solid base MgO can efficiently catalyze the ozonation of ammonium nitrogen. However, it is necessary to improve the problem of easy loss, difficult recovery, and low percentage of gaseous products. Here, MgO, amorphous Fe2O3,and γ-Al2O3 were selected as dopingcomponents and supports, resp., to prepare γ-Al2O3@Fe/Mg composite catalysts with abundant acidic-basicsites and oxygen vacancies. The results show that γ-Al2O3@Fe/Mg5 can efficiently catalyze the ozonation of ammonium nitrogen (98.73%) with 67.82% gaseous product selectivity under the conditions of initial pH = 7, catalyst dosage of 112.88 g/L, and ozone dosage of 2.4 mg/min. The doping of Fe2O3 and MgO with a weaker lattice oxygen binding energy improves the gaseous product selectivity. The mechanism of ammonium nitrogen removal for γ-Al2O3@Fe/Mg5 is revealed, especially the intrinsic contribution of acidic-basic sites and oxygen vacancies. The pH and active sites play different roles in ozone decomposition for NH4+ removal. Surface hydroxyl protonation on basic sites and oxygen vacancies and electron transfer on acidic sites are responsible for ozone decomposition to hydroxyl radicals. Moreover, γ-Al2O3@Fe/Mg5 exhibits good stability, few leaching ions, and can be settled in waterfor easy recovery. This study suggests that γ-Al2O3@Fe/Mg5 is a good candidate for the catalytic ozonation of ammonium nitrogen. After reading the article, we found that the author used Triacetonamine(cas: 826-36-8Electric Literature of C9H17NO)

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Electric Literature of C9H17NO

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

In 1965,Journal of Medicinal Chemistry included an article by Hermans, Bert; Daele, Paul van; Westeringh, Cornelis van de; Eycken, Cyriel van der; Boey, Jozef; Janssen, Paul A. J.. Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile. The article was titled 《4-Substituted piperidines. II. Reaction of 1-benzyl-4-cyano-4-tertiaryaminopiperidines with organometallic compounds》. The information in the text is summarized as follows:

cf. CA 61, 10652f. The reaction of 1-benzyl-4-cyano-4-tertiary-aminopiperidines with organomagnesium and organolithium compounds is described. Reaction of these α-amino nitriles with Grignard reagents results in replacement of the nitrile group, whereas with the organolithium compounds normal ketone formation takes place. The resulting products are debenzylated, whereafter other substituents are introduced. Some of the obtained products show central nervous system depressant activity. In the part of experimental materials, we found many familiar compounds, such as 4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile)

4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Reference of TriacetonamineOn May 18, 2021 ,《Interface-Promoted Direct Oxidation of p-Arsanilic Acid and Removal of Total Arsenic by the Coupling of Peroxymonosulfate and Mn-Fe-Mixed Oxide》 appeared in Environmental Science & Technology. The author of the article were Ke, Ming-Kun; Huang, Gui-Xiang; Mei, Shu-Chuan; Wang, Zhao-Hua; Zhang, Ying-Jie; Hua, Tian-Wei; Zheng, Li-Rong; Yu, Han-Qing. The article conveys some information:

As one of the extensively used feed additives in livestock and poultry breeding, p-arsanilic acid (p-ASA) has become an organoarsenic pollutant with great concern. For the efficient removal of p-ASA from water, the combination of chem. oxidation and adsorption is recognized as a promising process. Herein, hollow/porous Mn-Fe-mixed oxide (MnFeO) nanocubes were synthesized and used in coupling with peroxymonosulfate (PMS) to oxidize p-ASA and remove the total arsenic (As). Under acidic conditions, both p-ASA and total As could be completely removed in the PMS/MnFeO process and the overall performance was substantially better than that of the Mn/Fe monometallic system. More importantly, an interface-promoted direct oxidation mechanism was found in the p-ASA-involved PMS/MnFeO system. Rather than activate PMS to generate reactive oxygen species (i.e., SO4·-, ·OH, and 1O2), the MnFeO nanocubes first adsorbed p-ASA to form a ligand-oxide interface, which improved the oxidation of the adsorbed p-ASA by PMS and ultimately enhanced the removal of the total As. Such a direct oxidation process achieved selective oxidation of p-ASA and avoidance of severe interference from the commonly present constituents in real water samples. After facile elution with dilute alkali solution, the used MnFeO nanocubes exhibited superior recyclability in the repeated p-ASA removal experiments Therefore, this work provides a promising approach for efficient abatement of phenylarsenical-caused water pollution based on the PMS/MnFeO oxidation process.Triacetonamine(cas: 826-36-8Reference of Triacetonamine) was used in this study.

Triacetonamine(cas: 826-36-8) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Reference of Triacetonamine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Category: piperidinesOn October 6, 2005 ,《Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor》 was published in Journal of Medicinal Chemistry. The article was written by Deng, Hongfeng; Gifford, Andrew N.; Zvonok, Alexander M.; Cui, Guangjian; Li, Xiuyan; Fan, Pusheng; Deschamps, Jeffrey R.; Flippen-Anderson, Judith L.; Gatley, S. John; Makriyannis, Alexandros. The article contains the following contents:

A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochem. and imaging studies. 2-Iodophenyl-[1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl]methanone I (AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated racemic I and its enantiomers were prepared by radioiododestannylation of the tributyltin analogs in high yields, radiochem. purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [131I](R)-I as radioligand, racemic I exhibited a Ki value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiog. experiments with mouse brain sections, the distribution of radioiodinated I was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [131I](S)-I and none occurred with the (R)-enantiomer [131I](R)-I in sections from CB1 receptor knockout mice. Radioiodinated I thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors. After reading the article, we found that the author used 1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6Category: piperidines)

1-Methylpiperidine-2-carboxylic acid hydrochloride(cas: 25271-35-6) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem