19982-07-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Actamido-3,5-dimethyladmantane is used as a chemical intermediate for the synthesis of Memantine (M218000) for its neuroprotective properties. Memantine is particularly effective in treating moderate to severe Alzheimer's disease by regulating the activity of NMDA receptors in the brain, thus providing cognitive benefits and slowing the progression of the disease.
Additionally, due to its chemical properties as a white solid, 1-Actamido-3,5-dimethyladmantane may also be utilized in other applications within the pharmaceutical industry, such as the development of new drugs or formulations.

InChI:InChI=1/C14H23NO/c1-10(16)15-14-6-11-4-12(2,8-14)7-13(3,5-11)9-14/h11H,4-9H2,1-3H3,(H,15,16)

Upstream product

• 941-37-7 3,5-dimethyl-1-bromoadamantane 
• 75-05-8 acetonitrile 
• 60-35-5 acetamide 
• 702-79-4 1,3-dimethyladamantane 
• 707-37-9 1,3-dimethyl-5-adamantanol 
• 707-36-8 1-chloro-3,5-dimethyl-adamantane 
• 108-24-7 acetic anhydride 
• 41100-52-1 memantine hydrochloride 
• 75-36-5 acetyl chloride 
• 64-19-7 acetic acid 
• 74-90-8 hydrogen cyanide 
• 14670-94-1 3,5-dimethyl-1-adamantanecarboxylic acid 
• 101821-77-6 3,5-dimethyladamantan-1-yl nitrate 

Downstream Products

• 14931-70-5 1,3?diacetamido?5,7?dimethyladamantane 
• 41100-52-1 memantine hydrochloride 
• 707-37-9 1,3-dimethyl-5-adamantanol 
• 941-37-7 3,5-dimethyl-1-bromoadamantane 
• 19982-08-2 memantine* 
• 351329-87-8 N-(3-hydroxy-5,7-dimethyladamantan-1-yl)acetamide 
• 10347-01-0 1,3-dihydroxy-5,7-dimethyladamantane 
• 63971-25-5 3-amino-5,7-dimethyladamantan-1-ol 
• 356572-15-1 1,1-dibenzylamino-3,5-dimethyl-7-hydroxy-adamantane 
• 356572-20-8 1-(benzyloxycarbonyl)amino-3,5-dimethyl-7-hydroxyadamantane 
• 707-36-8 1-chloro-3,5-dimethyl-adamantane 
• 100063-87-4 N'--N-<3,5-dimethyl-adamantyl-(1)>-harnstoff 

Relevant academic research and scientific papers

New synthetic approach to memantine hydrochloride starting from 1,3-dimethyl-adamantane

A short and practical method for the synthesis of 1-amino-3,5-dimethyl- adamantane (Memantine hydrochloride) was established by using tertiary butyl alcohol under Ritter conditions to give 1-acetamido-3,5-dimethyl-adamantane. The 1-acetamido-3,5-dimethyl-adamantane is hydrolyzed using alkali to give free base which was then converted into its hydrochloride acid.

Process Safety Evaluation to Identify the Inherent Hazards of a Highly Exothermic Ritter Reaction Using Adiabatic and Isothermal Calorimeters

This paper describes the process safety studies that were carried out prior to the scale-up for the initial process containing the reaction of 1,3-dimethyladamantane with sulfuric acid and acetonitrile. The reaction temperature is set at 13 C followed by heating to 23 C for progress of the reaction. Thermal screening studies showed the exotherm onset to occur at 30 C, which is very close to the desired final process temperature, with high rate of temperature rise and pressure rise. Also understood was the better option for selecting the sequence of reagent addition, i.e., either acetonitrile or sulfuric acid. These thermal hazard evaluation results helped to redesign the process temperature at 38 ± 2 C, which was evaluated for safety aspects to prevent the untoward situation using an adiabatic calorimeter and an isothermal reaction calorimeter.

Two Step Cost-Saving Process for Industrial Scale Production of 1-Amino-3,5-dimethyladamantane Hydrochloride (An Anti-Alzheimer's Drug)

This work presents a predominant cost-saving process for the industrial scale synthesis of memantine hydrochloride (1) from 1,3-dimethyladamantane (2) by a two-step method in which both steps were carried out in one-pot. The conversion of 2 to N-(3,5dimethyladamantane-1-yl)acetylamide (3) was synthesized first in mixture of sulfuric acid 96-98% and nitric acid 64-65% at 25 oC for 2.5 h and then in acetonitrile at 40 oC for 3.5 h as a key step. The yield of this process reached to 98%. Next, the deacetylation of 3 with potasium hydroxide in mixture of water-ethylene glycol at 140 oC for 15 h to get memantine base which was then converted into memantine hydrochloride (1) by aq. HCl 14% (yield of 93%). Overall yield of this synthetic route was 91.65%. The advantages of this process is saving time, solvents, reagents and giving a higher yield as compared to reported procedures.

Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis

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.

Green preparation method of memantine

The method comprises the following steps: (1) mixing 1 - chlorine -3 and 5 - dimethyl adamantane with acetamide to obtain 1 -acetylamino -3 and 5 -dimethyladamantane. (2) The 1 -acetylamino -3, 5 -dimethyladamantane was deacetylated in a hot-water system to obtain a memantine. The preparation method provided by the invention is simple to operate. The method is safe, environment-friendly, high in yield and purity, cost-saving, low in production cost and beneficial to industrial production.

Preparation method of medicine for treating neurological function diseases

The invention discloses a preparation method of a medicine for treating neurological function diseases, which comprises the following steps: 1) adding 1-bromo-3,5-dimethyl adamantane, acetonitrile, acatalyst 1 and a catalyst 2 into a reaction kettle, stirring to react, adding a certain amount of water into the reaction solution, cooling to precipitate a solid, adding the solid into a certain proportion of an alcohol water solution, and carrying out hot melting and cold precipitation to obtain 1-acetamido-1,3-dimethyl adamantane; and (2) carrying out high-temperature reaction on 1-acetamido-1,3-dimethyl adamantane and sodium hydroxide in ethylene glycol, adding a certain amount of purified water, extracting by adopting dichloromethane, concentrating under reduced pressure, adding an ethylacetate hydrochloride solution into the concentrated solution, cooling to allow crystal growing, carrying out suction filtration, and drying to obtain memantine hydrochloride. According to the method,the catalyst 1 and the catalyst 2 are used as reaction catalysts, so that the operation risk caused by the use of concentrated sulfuric acid is avoided, the reaction time is shortened, and the side reaction is reduced. The post-treatment is simple, the reaction yield is high, and the product purity is good.

Memantine hydrochloride synthesis method

The invention provides a memantine hydrochloride synthesis method, and belongs to the technical field of medicine synthesis. The preparation method comprises the following steps: carrying out a substitution reaction on 1-bromo-3,5-dimethyladamantane and acetamide to obtain 1-acetamido-3,5-dimethyladamantane, mixing the 1-acetamido-3,5-dimethyladamantane, an alcohol and an alkali, carrying out an alcoholysis reaction to obtain 1-amino-3,5-dimethyladamantane, and finally carrying out an acidification reaction on the 1-amino-3,5-dimethyladamantane and hydrochloric acid to obtain memantine hydrochloride. According to the method of the invention, 1-bromo-3,5-dimethyl adamantane and acetamide are used as the starting raw materials, so the sources of the raw materials are wide, the use of acetonitrile is avoided, and no pollution is caused to the human body and the environment; the use of catalysts is avoided in the whole reaction process, the reaction product is easy to separate, and the yield of the obtained memantine hydrochloride is high; and the method is mild in reaction condition and suitable for industrial production.

Memantine hydrochloride impurity compound and preparation method thereof

The invention discloses a preparation method of a memantine hydrochloride impurity compound 1-nitro-7-hydroxy-3,5-dimethyl adamantane. According to the preparation method, 1-bromo-3,5-dimethyl adamantane is taken as a raw material and carries out a substitution reaction with acetamide in a molten state, then hydrolysis and salt forming happen in an alkaline environment, and finally the target product is prepared after hydroxylation and oxidation. The impurity compound is used as a reference substance for memantine hydrochloride quality control.

Preparation method of memantine hydrochloride impurity C

The invention discloses a preparation method of a memantine hydrochloride impurity C. The preparation method comprises a step of hydrolyzing an intermediate D under an acidic condition to obtain the impurity C. The preparation method has the advantages of novelty, usage of easily available raw materials, simple synthesis and good practicability.

Method for synthesizing N-alkanoyl memantine

The invention discloses a method for synthesizing N-alkanoyl memantine. The method comprises the steps that (a) memantine hydrochloride reacts with a formylation reagent or an acetylation reagent in areactive solvent; (b) after the reaction is completed, separation is carried out to obtain a target product. The method for synthesizing the N-alkanoyl memantine has the advantages that the operationis simple, the raw materials are easy to obtain, the preparation yield and product purity are higher, and the method is suitable for rapid preparation in analytical laboratories.