2213-43-6Relevant academic research and scientific papers
Kinetic and mechanistic study of N-aminopiperidine formation via the raschig process
Darwich,Elkhatib,Pasquet,Delalu
, p. 649 - 655 (2013)
Formation of N-aminopiperidine (NAPP) in the reaction of monochloramine with piperidine was studied by varying the reagents concentrations, pH and temperature. The study was carried out in diluted solutions, recording simultaneously monochloramine concentration by UV spectrophotometry at 243 nm and hydrazine concentration at 237 nm after treatment with formaldehyde. The presence of two competitive reactions: formation of NAPP and a complex parallel reaction limiting the yield of hydrazine, was established. Reaction products were characterized by GC/MS analysis. The rate constant of NAPP formation and activation parameters were determined, k1 = 56 × 10 -3 M-1 s-1 (25°C) and k1 = 9.3 × 106 exp(-46.5/RT) M-1 s-1, respectively. Pleiades Publishing, Ltd., 2013.
Kinetic modelling of synthesis of N-aminopiperidine from hydroxylamine-o-sulfonique acid and piperidine
Labarthe,Bougrine,Pasquet,Delalu
, p. 25 - 35 (2012)
A new route to synthesize N-aminopiperidine (NAPP) from hydroxylamine-O-sulfonique acid (HOSA) and piperidine was described. Kinetics of the reaction was investigated to optimize the conditions of the synthesis. Since the reaction is fast, this study was carried out in a diluted medium (10-3 to 10-2 mol/l). To determine the concentration of the reaction product, NAPP was allowed to react with formaldehyde and the product was analysed by UV and HPLC techniques. The formation of NAPP is consistent with the first-order reaction to two reagents, governed by the nucleophilic substitution via SN2 mechanism. Oxidation of NAPP by HOSA was identified as the main secondary reaction which consistently reduced the yield of NAPP. A number of differential equations were elaborated and solution of these equations serves to predict the behavior of the system as a function of the reagent concentrations, pH and temperature. From the corresponding mathematical treatment a unique implicit expression was derived that characterizes the reaction medium. It was found that the [PP] 0/[HOSA]0 molar ratio (p), the initial concentrations of [PP]0 and [HOSA]0, the ratio of rate constants k 2/k1 and temperature are the only parameters that affect the yield of NAPP from HOSA. The results calculated from this model are in good agreement with the experimental data and they can be used to determine the optimal conditions of the reaction. Pleiades Publishing, Ltd., 2012.
N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
supporting information, p. 17713 - 17721 (2021/11/10)
A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
Optimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria
Wu, Yachuang,Ding, Xiudong,Yang, Yifeng,Li, Yingxiu,Qi, Yinliang,Hu, Feng,Qin, Mingze,Liu, Yajing,Sun, Lu,Zhao, Yanfang
, (2019/10/23)
We previously discovered a series of novel biaryloxazolidinone analogues bearing a hydrazone moiety with potent antibacterial activity. However, the most potent compound OB-104 exhibited undesirable chemical and metabolic instability. Herein, novel biaryloxazolidinone analogues were designed and synthesized to improve the chemical and metabolic stability. Compounds 6a-1, 6a-3, 14a-1, 14a-3 and 14a-7 showed significant antibacterial activity against the tested Gram-positive bacteria as compared to radezolid and linezolid. Further studies indicated that most of them exhibited improved water solubility and chemical stability. Compound 14a-7 had MIC values of 0.125–0.25 μg/mL against all tested Gram-positive bacteria, and showed excellent antibacterial activity against clinical isolates of antibiotic-susceptible and antibiotic-resistant bacteria. Moreover, it was stable in human liver microsome. From a safety viewpoint, it showed non-cytotoxic activity against hepatic cell and exhibited lower inhibitory activity against human MAO-A compared to linezolid. The potent antibacterial activity and all these improved drug-likeness properties and safety profile suggested that compound 14a-7 might be a promising drug candidate for further investigation.
Selective reduction of N-nitroso aza-aliphatic cyclic compounds to the corresponding N-amino products using zinc dust in CO2–H2O medium
Yang, Weiqing,Lu, Xiang,Zhou, Tingting,Cao, Yongjing,Zhang, Yuanyuan,Ma, Menglin
, p. 780 - 783 (2018/10/20)
[Figure not available: see fulltext.] A new method for reduction of N-nitroso aza-aliphatic cyclic compounds employing zinc in pressurized CO2–H2O medium has been developed. H2O and NH4Cl were used as hydrogen donors, and reduction was performed under environmentally benign conditions. The presented approach allowed to obtain the respective N-amino products selectively and in excellent yields (up to 97%).
Synthesis and antibacterial activity evaluation of novel biaryloxazolidinone analogues containing a hydrazone moiety as promising antibacterial agents
Wu, Yachuang,Ding, Xiudong,Ding, Liang,Zhang, Yongsheng,Cui, Lei,Sun, Lu,Li, Wei,Wang, Di,Zhao, Yanfang
, p. 247 - 258 (2018/09/18)
A series of linezolid analogues containing a hydrazone moiety were designed, synthesized and evaluated for their antibacterial activity. Most compounds exhibited more potent antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens as compared with linezolid and radezolid. Compounds 9a, 9c, 9f, 9g, 10m and 10t were more potent against tested clinical isolates of MRSA, MSSA, VRE and LREF as compared to linezolid. Compound 9a exhibited comparable activity with linezolid against human MAO-A for safety evaluation and showed moderate metabolism in human liver microsome. The most promising compound 9a showed remarkable antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens with MIC value of 0.0675 mg/mL, respectively, which was 15- to 30-fold more potent than linezolid.
N - amino piperidine hydrochloride preparation method
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035-0037, (2017/08/25)
The invention relates to a preparation method of N-aminopiperidine hydrochloride. The preparation method comprises the steps: mixing piperidine with urea, and performing heating reflux reaction for 2-8 hours to obtain N-formamide piperidine; introducing chlorine gas for reaction for 1-2.5 hours when the dissolved N-formamide piperidine is at 0-20 DEG C, then carrying out Hoffmann rearrangement reaction under an alkaline condition to obtain N-aminopiperidine, reacting N-aminopiperidine with concentrated hydrochloric acid to obtain N-aminopiperidine hydrochloride. According to the preparation method of N-aminopiperidine hydrochloride, urea which serves as a raw material is low in cost and easy to obtain, highly toxic compounds such as hydrazine hydrate are not used, and nitro compounds with strong carcinogenicity are not produced in a synthetic process; and reaction conditions are mild, operation is simple, after-treatment is simple and convenient, and reaction yield is high.
Synthesis of Novel Saccharide Hydrazones
Ilisson, Mihkel,Tomson, Kristjan,Selyutina, Anastasia,Türk, Silver,M?eorg, Uno
supporting information, p. 1367 - 1373 (2015/06/18)
Synthesis of important heterocyclic hydrazine derivatives N-aminopyrrolidine, N-aminopiperidine, and N-aminoazepane from hydrazine hydrate and dihalogenides were examined and optimized. These heterocyclic hydrazine derivatives were used in condensation reactions with six different monosaccharides to form corresponding hydrazones. Biological evaluations of these novel compounds, which are simple acyclic nucleoside analogs, were done. L-Arabinose N-aminoazepane hydrazone showed minor anti-HIV activity, giving a starting point for further structural modifications. (Chemical Equation Presented).
Novel route to the synthesis of chalcogenolanes, chalcogenanes, and 1,2-dichalcogenaepanes
Levanova,Grabel'Nykh,Elaev,Russavskaya,Klyba,Albanov,Korchevin
, p. 1345 - 1352 (2014/07/21)
The saturated heterocyclic compounds C4H8Y, C 5H10Y, and C5H10Y2 (Y = Se or Te) have been prepared by the reaction of 1,4-dibromobutane or 1,5-dibromopentane with potassium chalcogenides. The novelty of the route consists of the use of the hydrazine hydrate-KOH system for the reductive generation of potassium selenide, telluride, diselenide or ditelluride from elemental chalcogens.
Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride
Zhang, Yan,Tang, Qiang,Luo, Meiming
supporting information; experimental part, p. 4977 - 4982 (2011/08/05)
N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.
