Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Inverse phase transfer catalysis preparation method for urapidil

A catalytic preparation, urapidil technology, applied in the direction of chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of difficult to achieve medicinal purity, product purity not provided and other problems, to achieve the effect of easy control of reaction conditions, shortened reaction time and good selectivity

Inactive Publication Date: 2013-04-17
ZHENGZHOU UNIV +1
View PDF2 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] (2) This method does not provide the purity of the product. When we repeated the reaction, we found that during the precipitation of the crude urapidil, the unreacted raw materials were accompanied by the precipitation of the product, making the product purity 85-90%. After crystallization, the purity is difficult to reach more than 98.5% of medicinal purity, therefore, the purity problem of the product needs to be solved

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
  • Inverse phase transfer catalysis preparation method for urapidil
  • Inverse phase transfer catalysis preparation method for urapidil
  • Inverse phase transfer catalysis preparation method for urapidil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1-(2-Methoxyphenyl)piperazine hydrochloride (5.67g, 0.025mol) was added to Na 2 CO 3 (5.27g, 0.050mol) and the mixture of 25ml water, be heated to 90 ℃, add 6-(3-chloropropyl)-1,3-dimethyluracil (5.00g, 0.022mol) in batches, Then add 0.2 g of β-cyclodextrin, complete the addition, react for 6 hours, add water, stir and cool, a white substance precipitates, filter under reduced pressure, and dry at room temperature to obtain 6.91 g of white powdery solid, with a yield of 82.6% and a purity of 99.91%. . m.p.136~138°C. 1 HNMR (CDCl 3 , 400 MHz) δ: 1.89-1.93(m, 2H, CH 2 ), 2.67-2.69 (m, 2H, CH 2 N), 2.77-2.78 (m, 4H, CH 2 N), 3.10-3.11(m, 4H, CH 2 N), 3.18-3.20 (m, 2H, CH 2 N), 3.33(s, 4H, CH 3 N), 3.42(s, 3H, CH 3 N), 3.89(s, 3H, CH 3 O), 4.80(s, H, CH=), 6.89-6.98(m, 3H, ArH), 7.04-7.08(m, H, ArH).

[0030] attached figure 1 The HPLC figure analysis result of urapidil standard substance is as follows:

[0031]

experiment example 1

[0032] The HPLC figure analysis result of experimental example 1 gained urapidil is as follows:

[0033]

Embodiment 2

[0035] 1-(2-methoxyphenyl)piperazine hydrochloride (12.84g, 0.056mol) was added into K 2 CO 3 (11.9g, 0.086mol) and the mixture of 50ml water, be heated to 96 ℃, add 6-(3-chloropropyl)-1,3-dimethyluracil (10g, 0.043mol) in batches, then Add 0.4 g of cetyltrimethylammonium bromide, after the addition is complete, react for 4 hours, add water, stir and cool, a white substance precipitates, filter under reduced pressure, and dry at room temperature to obtain 13.82 g of a white powdery solid, yield 83.0% , with a purity of 99.83%. Melting point and spectral data are the same as above.

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 discloses a preparation method for urapidil, and relates to an inverse phase transfer catalysis method for preparing urapidil, and belongs to the technical field of organic synthesis. The method comprises the following steps that: water is adopted as a solvent; an inorganic alkaline substance is adopted as an acid binding agent; 6-(3-chloropropyl)-1,3-dimethyluracil (I) reacts with 1-(2-methoxyphenyl)piperazine hydrochloride (II) in the presence of an inverse phase transfer catalyst to generate 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]-propyl]-amino]-1,3-dimethyl-uracil (III, urapidil). With the method, the high-selectivity and high-yield preparation of the urapidil can be realized; the prepared urapidil has high purity, wherein the purity of the urapidil is more than 99.5%;the conversion rate is high; the yield can reach 80%; the reaction conditions are mild; the selectivity is good; the post-treatment is simple; the method is environmental-friendly, and is suitable for the industrial production.

Description

technical field [0001] The invention relates to a preparation method of uradil, in particular to the preparation of uradil by a reverse phase transfer catalysis method, which belongs to the technical field of organic synthesis. Background technique [0002] Urapidil is a uracil substituted by benzoxinazole, its chemical name is 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]-propyl]-amino] -1, 3-Dimethyl-2, 4(1H, 3H)-pyrimidinedione, the English name is 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]amino]-1 ,3-dimethyl-uracil, the structural formula is: [0003] [0004] The trade names of urapidil hydrochloride are ladenidine, Ebrantil, and lixidine. Its mechanism of action is 1 Receptor blockers and weaker beta blockers have both peripheral and central effects. By blocking peripheral postsynaptic alpha 1 Dilate blood vessels after the receptor, and directly excite the central 5-HT 1A The receptor reduces the sympathetic feedback modulation of the medullary cardiovascu...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/545B01J31/06B01J31/02
Inventor 李雯朱松林马晓青陈水库朱成功杜孟洪余卫晓姬力莎袁坤黄占海
Owner ZHENGZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com