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

Preparation method of 1,2-cyclopentane dicarboximide

A technology of cyclopentanedicarboxamide and cyclohexanone carboxamide, which is applied in the field of chemical synthesis of organic 1,2-cyclopentanedicarboxamide, can solve the problems of high temperature energy consumption equipment, high raw material cost, The total yield is only a problem, to achieve the effect of reducing the discharge of the three wastes, reducing the production cost and improving the yield

Inactive Publication Date: 2013-01-02
山东洪智生物科技有限公司
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, when the method changes from acid to acid anhydride, the raw material used is acetic anhydride, and the acid anhydride will be carbonized when purified at high temperature, the yield is low, and the cost of raw materials is high.
In addition, the domestic patent (CN1876636A) reports that 1,2-cyclopentane dicarboxamide is used as raw material, and the yield is 82.15% through salt formation and cyclization. Although the yield has increased, there are high temperature energy consumption and Special requirements for equipment, and the 1,2-cyclopentane dicarboxamide raw material mentioned in the patent is generally synthesized from α-bromocyclohexanone carboxamide, and the total yield is only 65.72%

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 of 1,2-cyclopentane dicarboximide
  • Preparation method of 1,2-cyclopentane dicarboximide
  • Preparation method of 1,2-cyclopentane dicarboximide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: A kind of preparation method of 1,2-cyclopentane dicarboximide, carries out following steps successively:

[0027] In a 250mL three-neck flask equipped with mechanical stirring, add 70ml of methanol and 30g of α-bromocyclohexanone formamide, cool down to 0-5°C, slowly add dropwise 50ml of methanol solution containing 14.8g of methanol sodium salt, after the dropwise addition , keep stirring for 30 minutes.

[0028] After the reaction is over, the device should be used for ordinary distillation to remove the alcohol solvent, then start to heat up to 180~220°C, carry out vacuum distillation to remove the generated solvent, add 150ml of ethyl acetate after cooling, add 5g of activated carbon, and heat to reflux for 1 hours, filtered while it was hot, and the filtrate was crystallized at room temperature to obtain the product 1,2-cyclopentanedicarboximide, which was vacuum-dried at 40°C for 1 hour to obtain 14.58 g of the product with a yield of 76.55%.

Embodiment 2

[0029] Embodiment 2: a kind of preparation method of 1,2-cyclopentane dicarboximide, carry out following steps successively:

[0030] In a 250mL three-neck flask equipped with mechanical stirring, add 100ml methanol and 30g α-bromocyclohexanone formamide, cool down to 0-5°C, slowly add dropwise 20ml methanol solution containing 7.4g methanol sodium salt, after the dropwise addition , keep stirring for 30 minutes.

[0031] After the reaction is over, the device should be used for ordinary distillation to remove the alcohol solvent, then start to heat up to 180~220°C, carry out vacuum distillation to remove the generated solvent, add 150ml of ethyl acetate after cooling, add 5g of activated carbon, and heat to reflux for 1 hour, filtered while hot, and the filtrate was crystallized at room temperature to obtain the product 1,2-cyclopentane dicarboximide, which was vacuum-dried at 40° C. for 1 hour to obtain 13.79 g of the product with a yield of 72.41%.

Embodiment 3~11

[0032] Embodiments 3-11: By changing the solvent, alcohol sodium salt concentration, and reaction time in the above-mentioned embodiment 1 or 2, corresponding embodiments 3-11 can be obtained. The specific content is shown in Table 1, and the product yield of each embodiment gained is shown in Table 1.

[0033] The concrete data of table 1, embodiment 3-11

[0034]

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a preparation method of 1,2-cyclopentane dicarboximide disclosed as a chemical structural formula on the right. The preparation method comprises the following steps: reacting the raw material alpha-bromocyclohexanone formamide with alcohol and alcohol sodium salt at low temperature for 0.5-1.5 hours, wherein the mol ratio of alpha-bromocyclohexanone formamide to alcohol sodium salt is 1:(1-2); and after the reaction finishes, removing the solvent, continuing heating to 180-220 DEG C to carry out condensation, removing the alcohol solvent, and recrystallizing with a proper solvent to obtain the 1,2-cyclopentane dicarboximide. The 1,2-cyclopentane dicarboximide prepared by the method disclosed by the invention can be used as an intermediate of gliclazide; and compared with the 1,2-cyclopentane dicarboximide prepared by the traditional ammonia water technique, the 1,2-cyclopentane dicarboximide prepared by the method disclosed by the invention has the advantages of high yield, low energy consumption, less wastewater and the like, and provides a feasible technical route for industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis method of organic 1,2-cyclopentanedicarboximide, which belongs to the field of chemical synthesis. Background technique [0002] 1,2-Cyclopentanedicarboximide is an important intermediate for the preparation of Gliclazide. Gliclazide is a second-generation sulfonylurea oral hypoglycemic drug used for the treatment of non-insulin-dependent diabetes (type II diabetes), which has dual effects of lowering blood sugar and improving blood coagulation function, and has mild lipid metabolism Improvement effect, few side effects, has been widely used clinically. [0003] The synthesis of gliclazide can be prepared by the reaction of N-amino-3-azabicyclo[3.3.0]octane and ethyl p-toluenesulfonyl formate, while 1,2-cyclopentane dicarboximide is It is a key intermediate for the synthesis of N-amino-3-azabicyclo[3.3.0]octane, and the yield of this intermediate is low. Gliclazide usually uses cyclohexanone and urea as ...

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 Applications(China)
IPC IPC(8): C07D209/52
Inventor 范兴山王飞龙王凤滩段义杰张朋
Owner 山东洪智生物科技有限公司
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