Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of production technology of n-benzyl-4-piperidinecarboxylic acid methyl ester

A technology for the production of piperidinecarboxylic acid and its production process is applied in the field of production process of methyl N-benzyl-4-piperidinecarboxylate, which can solve the problems of high environmental protection pressure, a purity of only 92%, and the inability to apply mechanically, and achieve quality control. The effect of stable efficiency, low raw material price, and shortened reaction time

Active Publication Date: 2021-04-30
山东诚汇双达药业有限公司
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

US 20020099035 discloses that methyl 4-piperidinecarboxylate is used as a raw material to react with benzyl bromide, and methanol is used as a solvent. The molar yield of methyl N-benzyl-4-piperidinecarboxylate is 97%, which is the highest reported in the literature, but the purity is only 92%, and the solvent methanol reaction can not be applied mechanically
[0005] There are several problems in the above preparation method: (1) The solvent DMF, ethanol, acetone or acetonitrile is miscible with water, and after the reaction is completed, water is added for treatment, so it is difficult to realize the solvent application after the reaction; (2) The molar yield is relatively low at about 80%; ( 3) The price of benzyl bromide as a raw material is high; (4) The molar ratio of benzyl bromide to methyl 4-piperidinecarboxylate is 1.3:1, and the excess of benzyl bromide is large; several problems make the process conditions unfavorable for industrial production; resulting in N- The raw material cost of benzyl-4-piperidinecarboxylate is relatively high, and the inappropriate use of solvents poses a greater pressure on environmental protection

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]The 1000L reactor was added to 286.36 kg of dichloromethane, and 4-piperidinic acid methyl 143.18 kg and triethylamine were added to 111.31 kg, and 139.24 kg was added dropwise 10 to 20 ° C. The drip slowly warmed to the reflux reaction for 6 hours, the raw material reaction was completely cooled to 20 ~ 30 ° C, add 150 kg of water washing 30 minutes, the organic layer was dried, filtered, the filtrate was concentrated to N-benzyl-4-piperidylmethyl ester 226.78kg; molar yield 97.2%, purity 99.54%.

Embodiment 2

[0031]1,2-dichloroethane was added to 429.54 kg of 1,2-dichloroethane, and 143.18 kg and triethylamine were added to 121.43 kg and triethylamine under stirring, 10 to 20 ° C were added dropwise to 139.24 kg. The drip slowly warmed to the reflux reaction for 1.5 hours, the feedstock reaction was completely cooled to 20 ~ 30 ° C, add 150 kg of water washing 30 minutes, the organic layer was dried, filtered, the filtrate was concentrated to N-benzyl-4-piperidinylmethyl ester 228.88kg; molar yield 98.1%, purity 99.65%. The recovered 1,2-dichloroethane is used for the next reaction.

Embodiment 3

[0033]In Example 2 was incorporated in Example 2, 1,2-dichloroethane was recovered in Example 2, adding 69.54 kg of new 1,2-dichloroethane, adding 4-piperidin formate 143.18kg and three by stirring. The amine was 121.43 kg, 10 to 20 ° C, 10 to 20 ° C, 10 to 20 ° C. The drip slowly warmed to the reflux reaction for 1.5 hours, the feedstock reaction was completely cooled to 20 ~ 30 ° C, add 150 kg of water washing 30 minutes, the organic layer was dried, filtered, the filtrate was concentrated to N-benzyl-4-piperidinylmethyl ester 230.04kg; molar yield 98.6%, purity 99.61%. The recovered 1,2-dichloroethane is used for the next reaction.

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 belongs to the technical field of medicine and chemical industry, and in particular relates to a production process of methyl N-benzyl-4-piperidinecarboxylate. The process comprises the following steps: methyl 4-piperidinecarboxylate and benzyl chloride are reacted in a reaction solvent under the condition of an acid-binding agent, the raw materials are reacted and cooled and washed with water, the organic layer is dried, filtered, and concentrated to obtain N-benzyl-4 ‑Methyl piperidinecarboxylate. The process uses 1,2-dichloroethane as a solvent for reaction, and the concentrated 1,2-dichloroethane can be recycled, which is environmentally friendly and greatly reduces the cost of raw materials.

Description

Technical field[0001]The present invention belongs to the technical field of medical chemical technology, and more particularly to the production process of methyl N-benzyl-4-piperidinicate.Background technique[0002]Methyl n-benzyl-4-piperidinicate is an important medical and chemical intermediate, which is widely concerned in pharmaceuticals and chemicals. In the pharmaceutical sector, methyl n-benzyl-4-piperidotenic acid is an important intermediate for the treatment of elderly dementia. N-benzyl-4-piperidotoate methyl ester chemical molecular formula C14Hide19NO2, Molecular weight 233.31, CAS number 10315-06-7; its structural formula[0003].[0004]Document J Med Chem, 1996, 39 (3): 749-756. Report is carried out in DMF for the solvent, potassium carbonate is a base, and the reaction temperature and time have not been reported, the obtained N-benzyl-4-piperidotylmethylmola The yield was 70%. WO 9909073 solid phase synthesis N-benzyl-4-piperidinicate is not suitable for industrial pr...

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): C07D211/62
CPCC07D211/62
Inventor 李跃东葛正全杨茂峰谭光明苗启来
Owner 山东诚汇双达药业有限公司
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