Check patentability & draft patents in minutes with Patsnap Eureka AI!

Preparation method for mexiletine hydrochloride impurity C

A technology for mexiletine hydrochloride and impurities, which is applied in the field of preparation of mexiletine hydrochloride impurity C, can solve the problems that the synthesis route and preparation method of impurities are not disclosed, and achieve the effects of high product purity, convenient operation and high stability

Active Publication Date: 2020-11-24
CHANGZHOU YABANG PHARMA
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Mexiletine hydrochloride impurity C is recorded in the quality standard of mexiletine hydrochloride in European Pharmacopoeia 9.0 edition, is referred to as impurity C for short, and the structure of impurity C is shown in formula I, and the synthesis route and preparation method for this impurity are not seen in the prior art public

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method for mexiletine hydrochloride impurity C
  • Preparation method for mexiletine hydrochloride impurity C
  • Preparation method for mexiletine hydrochloride impurity C

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: intermediate preparation

[0029] Take 0.5g (1.0eq) of 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl, 0.86g (3.0eq) of potassium carbonate, 0.57g (3.0eq) of monochloroacetone, Add it to 10ml of N,N-dimethylformamide, and heat up to 80°C for 2h. Cool to 25°C, add 10ml of water, extract the organic phase once with 20ml of ethyl acetate, separate the liquid to obtain the organic phase, wash the organic phase twice with 10ml of water, dry with 2g of anhydrous sodium sulfate, and concentrate. 0.5 g of the crude product was obtained with a yield of 68%.

Embodiment 2

[0030] Embodiment 2: intermediate preparation

[0031] Get 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl 10g (1.0eq), potassium carbonate 17g (3.0eq), monochloroacetone 11.4g (3.0eq), add to In 100ml of N,N-dimethylformamide, the temperature was raised to 80°C for 4h. After cooling, 100ml of water was added, and the organic phase was extracted once with 200ml of ethyl acetate to obtain an organic phase. The organic phase was washed twice with 100ml of water, then dried with 20g of anhydrous sodium sulfate, and concentrated. A solid was obtained, which was beaten once with 50 ml of petroleum ether, and air-dried at 50° C. to obtain 10 g of a crude product, with a yield of 68%.

[0032] Example 1 and Example 2 are the preparation of intermediates, and the data in Example 1 to Example 2 are magnified 20 times to show that the synthesis method in the present invention is feasible.

Embodiment 3

[0033] Embodiment 3: preparation of mexiletine hydrochloride impurity C

[0034] Take 1g (1.0eq) of the intermediate and add it to the reaction kettle, then add 50ml ammonia methanol and 0.5g Raney nickel, vacuumize, feed hydrogen, replace three times, and then feed hydrogen until the pressure inside the kettle is 1.0 ~ 1.2Mpa , start stirring, heat up to 100-110°C, heat-preserve and pressurize for 1 hour, cool to 25°C, and filter with suction. The filtrate was obtained and concentrated to dryness. Column chromatography (MeOH / DCM=1 / 15) gave 0.1 g of solid. The above solid was added to 1 ml of HCl(g) / EA solution. Stir at room temperature for 10 min, and concentrate to dryness to obtain 0.1 g of solid.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the technical field of chemical synthesis and particularly relates to a preparation method for a mexiletine hydrochloride impurity C. The preparation method comprises the following steps: subjecting 3,3',5,5'-tetramethyl-4,4'-dihydroxybiphenyl and monohalogenated acetone to a reaction in an organic solvent in the presence of an alkaline compound, and carrying out separating, so as to obtain an intermediate; and subjecting the intermediate to catalytic hydrogenation, carrying out an ammonization reaction in an organic solvent of ammonia, carrying out purifying, and carrying out hydrochloride forming, thereby producing a compound I. The technical scheme employed by the invention has the beneficial effects that operations are convenient, reaction conditions are controllable, the stability is high, and the purified product is relatively high in purity; and the compound represented by a formula I can be used for providing a satisfactory impurity control for qualitycontrol on mexiletine hydrochloride.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of mexiletine hydrochloride impurity C. Background technique [0002] Mexiletine Hydrochloride (Mexiletine Hydrochloride), the chemical name is (±) 1-(2,6-dimethylphenyl)-2-propanamine hydrochloride, and the molecular formula is C 11 h 18 ClNO, the molecular weight is 215.72. Mexiletine hydrochloride is a white or off-white crystalline powder; almost odorless, slightly bitter taste; easily soluble in water, slightly soluble in ethanol, acetone, insoluble in ether; easy to absorb moisture in the air. The structure of mexiletine hydrochloride is similar to that of lidocaine. It was initially found to have anticonvulsant effect. Later, it was proved that the drug has a good curative effect on arrhythmia caused by coronary artery ligation. At present, it is mainly used clinically to treat ventricular premature beats, Tachycardia, ventricular fibrill...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C217/20C07C213/02
CPCC07C213/02C07C217/20
Inventor 陶锋马绍明陈松王德祥夏正君
Owner CHANGZHOU YABANG PHARMA
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com