351329-88-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(3,5-DiMethyladaMantan-1-yl)forMaMide is used as an impurity reference for Memantine (M218000) in the pharmaceutical industry. Its identification and quantification are crucial for ensuring the quality, safety, and efficacy of Memantine-based medications. As an impurity, it is essential to monitor and control its levels in the final drug product to meet regulatory standards and maintain therapeutic integrity.
Used in Quality Control and Research:
In the fields of quality control and research, N-(3,5-DiMethyladaMantan-1-yl)forMaMide serves as a reference compound for developing and validating analytical methods, such as high-performance liquid chromatography (HPLC) or other chromatographic techniques. These methods are employed to detect, quantify, and control the presence of this impurity in Memantine drug products, ensuring compliance with pharmacopeial guidelines and industry best practices.
Used in Drug Development:
During the drug development process, N-(3,5-DiMethyladaMantan-1-yl)forMaMide can be utilized as a starting material or intermediate in the synthesis of novel Memantine-related compounds. Researchers may explore its potential for modifying the pharmacological properties of Memantine or developing new therapeutic agents with improved efficacy, safety, or pharmacokinetic profiles.

InChI:InChI=1S/C13H21NO/c1-11-3-10-4-12(2,6-11)8-13(5-10,7-11)14-9-15/h9-10H,3-8H2,1-2H3,(H,14,15)

Upstream product

• 941-37-7 3,5-dimethyl-1-bromoadamantane 
• 77287-34-4 formamide 
• 707-36-8 1-chloro-3,5-dimethyl-adamantane 
• 702-79-4 1,3-dimethyladamantane 
• 707-37-9 1,3-dimethyl-5-adamantanol 
• 101821-77-6 3,5-dimethyladamantan-1-yl nitrate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 64-18-6 formic acid 
• 41100-52-1 memantine hydrochloride 
• 68-12-2 N,N-dimethyl-formamide 
• 1262660-45-6 o-nitrophenyl formate 
• 1865-01-6 (4-nitrophenyl) formate 

Downstream Products

• 19982-08-2 memantine* 
• 41100-52-1 memantine hydrochloride 

Relevant academic research and scientific papers

An improved synthesis of memantine hydrochloride: Anti-Alzhelmer's drug

An economical new process route has been developed for the large-scale synthesis of memantine hydrochloride (1) an anti-Alzheimer's drug. The procedure involves the conversion of 1,3-dimethyl adamantane (2) to formamide intermediate 8 as a key step, followed by hydrolysis to (1-amino-3,5-dimethyl adamantane) hydrochloride (1) in good yield.

PROCESS FOR PREPARATION OF MEMANTINE

The present invention provides an improved process of manufacturing 1-Bromo-3,5-dimethyladamantane compound of formula-IV starting from 1,3-dimethyladamantane that avoids use of liquid bromine and minimizes the use of hazardous chemicals. The present invention also provides use of 1-Bromo-3,5-dimethyladamantane prepared by the process of present invention in the process of producing Memantine hydrochloride and pharmaceutical compositions thereof.

Preparation method of memantine hydrochloride (by machine translation)

The preparation method of the memantine hydrochloride, comprises the following steps,1 - bromo - 333355-dimethyladamantane, used as a hydrolysis reagent, to hydrolyze the formamide group to obtain a finished product of memantine hydrochloride . The method disclosed by the invention is relatively mild in preparation conditions and low in cost, obtained by hydrolysis of the amino substituent, by using formamide as a hydrolysis reagent . The method, further comprises the following steps: preparing a finished product of, memantine hydrochloride by using, a sodium hydroxide solution as a, hydrolysis reagent. (by machine translation)

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.

Improvement method for synthesis process of memantine hydrochloride

The invention discloses an improvement method for a synthesis process of memantine hydrochloride; with 1,3-dimethyl adamantane as a raw material, 3,5-dimethyl-1-adamantanol is obtained through a bromination reaction and a hydrolysis reaction; 3,5-dimethyl-1-adamantanol is subjected to a chlorination reaction to obtain 1-chloro-3,5-dimethyl adamantane; and 1-chloro-3,5-dimethyl adamantane is subjected to an ammoniation reaction, acid hydrolysis and salt formation, and the target product of methamine hydrochloride is produced, wherein in the bromination reaction, the reaction molar ratio of 1,3-dimethyl adamantane and bromine is 1:1.1, the reaction is performed in dichloroethane, and after the hydrolysis reaction, an organic phase is separated and washed to remove bromine and washed and dried, and an obtained solution is directly used for a next reaction. The improvement method provided by the invention can improve the yield, increase reaction safety and reduce waste and waste water.

PROCESS FOR MANUFACTURING ADAMANTANE DERIVATIVES WITH HIGH YIELD

The present invention pertains to process for the amidation of a substituted 1-bromo-adamantane comprising a step (0) of reacting a substituted adamantane with an excess of bromine to obtain a 1-bromo-adamantane and a step (i) of reacting said substituted 1-bromo-adamantane with an amide, wherein the substituted 1-bromo-adamantane is used in the form of a mixture comprising bromine as obtained in step (0), wherein in step (0) a bromine: substituted adamantane molar ratio of from [2.5:1] to less than [5:1] is employed.

A PROCESS FOR PREPARING MEMANTINE

The present invention relates to a process for preparing memantine, or a pharmaceutically acceptable salt thereof (e.g., memantine hydrochloride), which is substantially free of impurities.

Process for the manufacture of memantine and intermediate product

The present invention relates to a process for manufacturing N-Formyl-1-amino-3,5-dimethyladamantane, an intermediate product in the overall process of producing 1-Amino-3,5-dimethyladamantane hydrochloride (Memantine). Therein, the process comprises the following steps: (a) reacting 1,3-dimethyladamantane with an acid mixture comprising concentrated sulfuric acid and concentrated nitric acid, wherein 1 to 6 volume parts of sulfuric acid are used per weight part of 1,3-dimethyladamantane; (b) reacting the solution from step (a) with an amount of formamide varying from 1 to 5 molar equivalents per mole of deprotonated 1,3-dimethyladamantane from step (a) to obtain N-Formyl-1-amino-3,5-dimethyladamantane. In step (b), the molar ratio of total acid, i.e. the molar amount of sulfuric acid and the molar amount of nitric acid taken together versus the molar amount of formamide is at least 1.5 and that the temperature is at least 50°C. The present invention also relates to the overall process of manufacturing Memantine from 1,3-dimethyladamantane by means of hydrolyzing the intermediate NFORM.