880-52-4Relevant articles and documents
Comparative theoretical and experimental analysis of hydrocarbon σ-radical cations
Novikovskii,Gunchenko,Prikhodchenko,Serguchev,Schreiner,Fokin
, p. 1293 - 1299 (2011)
The structures of σ-radical cations formed by ionization of adamantane, twistane, noradamantane, cubane, 2,4-dehydroadamantane, and protoadamantane were optimized at the B3LYP, B3LYP-D, M06-2X, B3PW91, and MP2 levels of theory using 6-31G(d), 6-311+G(d,p), 6-311+G(3df,2p), cc-PVDZ, and cc-PVTZ basis sets. On the whole, single-configuration approximations consistently describe the structure and transformations of the examined σ-radical cations. The best correlations (r = 0.97-0.98) between the calculated adiabatic ionization potentials and experimental oxidation (anodic) potentials of hydrocarbons were obtained in terms of B3PW91 approximation. Pleiades Publishing, Ltd., 2011.
1-Acetamidoadamantane
Proehl, Hans-Heinrich,Blaschette, Armand,Jones, Peter G.
, p. 1434 - 1436 (1997)
In the title compound, C12H19NO, the bond lengths and angles are closely similar to those of two cagesubstituted 1-acetamidoadamantanes. The molecules are linked into polymeric chains through a weak N-H...O hydrogen bond [H...O 2.04 (2), N...O 2.928 (2) A and N-H...O 168 (1)°].
Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis
Narobe, Rok,Murugesan, Kathiravan,Schmid, Simon,K?nig, Burkhard
, p. 809 - 817 (2022/01/15)
Recent years have witnessed important progress in synthetic strategies exploiting the reactivity of carbocations via photochemical or electrochemical methods. Yet, most of the developed methods are limited in their scope to certain stabilized positions in molecules. Herein, we report a metal-free system based on the iodine (I/III) catalytic manifold, which gives access to carbenium ion intermediates also on electronically disfavored benzylic positions. The unusually high reactivity of the system stems from a complexation of iodine (III) intermediates with BF3. The synthetic utility of our decarboxylative Ritter-type amination protocol has been demonstrated by the functionalization of benzylic as well as aliphatic carboxylic acids, including late-stage modification of different pharmaceutical molecules. Notably, the amination of ketoprofen was performed on a gram scale. Detailed mechanistic investigations by kinetic analysis and control experiments suggest two mechanistic pathways.
Preparation method of amantadine
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Paragraph 0112-0123, (2021/06/13)
The invention discloses a preparation method of amantadine, which belongs to the technical field of organic chemical synthesis, and is characterized by comprising the following steps: taking a compound adamantane as an initial raw material, generating an intermediate 1-acetamido adamantane in the presence of acetonitrile, a polyion liquid PIL catalyst and sulfuric acid, and then hydrolyzing the intermediate into amantadine in a system of alcohol and alkali. The preparation method is environment-friendly, post-treatment is convenient, the use amount of sulfuric acid and acetonitrile is greatly reduced through the catalyst polyion liquid, and post-treatment is simple. The ionic liquid catalyst can be recycled, so that the cost is greatly saved, and the method is suitable for large-scale industrial production.
Method for preparing 3-acetamido-1-adamantanol
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Paragraph 0026; 0030; 0034, (2021/01/29)
The invention discloses a method for preparing 3-acetamido-1-adamantanol, and belongs to the technical field of chemical synthesis. The method comprises the following steps: using adamantane as a starting raw material, adding acetonitrile into fuming sulphuric acid to carry out amidation reaction, and carrying out HNO3 nitration reaction, KOH/H2O alkaline hydrolysis reaction and separation and purification to obtain the 3-acetamido-1-adamantanol. According to the method, the 3-acetamido-1-adamantanol is prepared by adopting a sulfuric acid system continuous utilization method so that the generation of waste acid is reduced, and the method is green, environment-friendly, low in raw material price, rapid in reaction, high in yield, high in purity, simple in process and suitable for industrial production.
Method for continuously preparing N-acetyl amantadine
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Paragraph 0026-0049, (2021/04/21)
The invention relates to the technical field of synthesis of N-acetyl amantadine, in particular to a method for continuously preparing N-acetyl amantadine. The method for continuously preparing N-acetyl amantadine comprises the following steps: carrying out continuous reaction in a micro-channel reactor by using adamantane, acetonitrile and acid as raw materials and halogenated alkane as a solvent, wherein the injection speed of adamantane, acetonitrile and halogenated alkane is recorded as V1, the injection speed of the acid is recorded as V2, and (V1+V2)* residence time=liquid holdup is satisfied.
Synthetic method of amantadine hydrochloride (by machine translation)
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Paragraph 0115-0119; 0145-0149; 0157-0161; 0169-0184, (2020/05/29)
Compared, the prior art . the synthesis method: the amantadine hydrochloride has an important clinical value and market value Ritter, and the synthesis process, of the hydrochloric acid adamantanamine, effectively improves the industrial application potential, of the hydrochloric acid adamantane hydrochloride synthesis process as, by adopting a special process and a component, on the one hand for preparation of the medicine, for treating and preventing viral infection, through hydrolysis and purification on the other hand, and effectively solves the problem, of environmental pollution in the synthesis process of the hydrochloric acid adamantanamine by adopting a special process and a component technology; through hydrolysis and purification on an aspect, through hydrolysis and, purification of components . The method mainly, comprises, steps of preparation of an amantadine hydrochloride synthesis process by using a special process and a method. (by machine translation)
Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid
Kireeva, A. V.,Nakhod, M. A.,Novakov, I. A.,Orlinson, B. S.,Pichugin, A. M.,Porkhun, V. I.,Potaenkova, E. A.,Savelyev, E. N.,Vostrikova, O. V.,Zavyalov, D. V.
, p. 1096 - 1101 (2020/07/25)
Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94percent). This enabled the synthesis of adamantylaminoarenes in 83–99percent yields and with 95–99percent purity.
IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
Talukdar, Ranadeep
supporting information, p. 5303 - 5308 (2020/04/17)
An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
Synthetic method of amantadine hydrochloride
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Paragraph 4-6, (2019/02/17)
The invention discloses a synthetic method of amantadine hydrochloride. The synthetic method comprises the following steps: preparation of 1-acetamido adamantane, preparation of amantadine and preparation of amantadine hydrochloride, wherein the preparation of the 1-acetamido adamantine comprises the steps of dropwise adding acetonitrile into 20 percent of fuming sulfuric acid, adding a nickel-rhodium bimetallic catalyst and adamantane, rising the temperature, slowly and dropwise adding ice salt water for diluting after completing reaction, extracting, washing, drying, and evaporating and removing a solvent, thus obtaining the 1-acetamido adamantine. The synthetic method disclosed by the invention has the beneficial effects that the alumina supported nickel-rhodium bimetallic catalyst is used for catalyzing acetyl ammoniation reaction of the adamantane, nickel and rhodium are in synergistic effect, the catalytic activity is enhanced, reaction is facilitated to proceed, meanwhile, occurrence of side effects is inhibited, and the yield of a target product is increased; a bromine raw material is prevented from being used, corrosion of bromine to equipment and pollution of the bromineto environment can be avoided, the environmental protection property is good, and the synthetic method is mild in condition, simple and feasible in technology and high in product yield.
