The synthetic method of roxatidine intermediate 3-(1-piperidinylmethyl)phenol

A technology of piperidinyl methyl and roxatidine, which is applied in the field of synthesis of rosatidine intermediate 3-phenol, can solve the problems of large amount of three wastes, dangerous operation and high cost, and achieves less generation of three wastes and reduced Preparation cost, novel effect of route

Active Publication Date: 2018-01-12
ANHUI HERYI CHEM
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the diazotization reaction involved, there is a certain risk of operation, and the production of three wastes is large, the yield is low, and the cost is high

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
  • The synthetic method of roxatidine intermediate 3-(1-piperidinylmethyl)phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Synthesis of m-methoxybenzyl chloride: 100g m-methoxybenzyl alcohol is added in 160ml thionyl chloride, the mixture is heated to reflux reaction for 1h, after the reaction is over, excessive thionyl chloride is recovered under reduced pressure to obtain 104g m-methoxybenzyl chloride oil, GC detection purity above 98%;

[0017] (2) Synthesis of 3-(1-piperidinylmethyl)anisole: add 100ml piperidine, 15g sodium borohydride and 100ml absolute ethanol to the oily substance obtained in the upward step, and the mixture is heated to reflux for 8 hours, and the reaction ends Recover ethanol under reduced pressure, then add 200ml of water to the residue, and add dilute hydrochloric acid to adjust the pH value to 3-4, take the water phase and add 100ml ethyl acetate for extraction, then take the resulting aqueous layer and adjust the pH value to 9 with ammonia water, and The precipitated oil was separated, and 131g of 3-(1-piperidylmethyl)anisole oil was obtained after washing ...

Embodiment 2

[0020] (1) Synthesis of m-methoxybenzyl chloride: 100g m-methoxybenzyl alcohol is added in 160ml thionyl chloride, the mixture is heated to reflux reaction for 1h, after the reaction is over, excessive thionyl chloride is recovered under reduced pressure to obtain 106g m-methoxybenzyl chloride oil, GC detection purity above 98%;

[0021] (2) Synthesis of 3-(1-piperidinylmethyl)anisole: add 100ml piperidine, 15g sodium borohydride and 100ml absolute ethanol to the oily substance obtained in the upward step, and the mixture is heated to reflux for 8 hours, and the reaction ends Recover ethanol under reduced pressure, then add 200ml of water to the residue, and add dilute hydrochloric acid to adjust the pH value to 3-4, take the water phase and add 100ml ethyl acetate for extraction, then take the resulting aqueous layer and adjust the pH value to 9 with ammonia water, and The separated oily matter was separated, and 135g of 3-(1-piperidylmethyl)anisole oily matter was obtained a...

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 method for synthesizing Roxatidine intermediate 3-(1-piperidinyl methyl) phenol and relates to the technical field of organic synthesis. M-anisyl alcohol which is cheap and easy to obtain is used as a raw material and firstly reacts with sulfinyl chloride to produce m-methoxybenzyl chloride, then the m-methoxybenzyl chloride reacts with piperidine to produce 3-(1-piperidinyl methyl) anisole, and finally demethoxylation is performed in hydrobromic acid to obtain the target product 3-(1-piperidinyl methyl) phenol. The route is clear, the yield is high, the amount of produced waste water, gas and residues is small, the recycling of solvent can be realized, the preparation cost is reduced and the cost is less than half of the cost of the original route.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing roxatidine intermediate 3-(1-piperidinylmethyl)phenol. Background technique: [0002] 3-(1-piperidinylmethyl)phenol is an important organic chemical intermediate, which is widely used in the fields of pesticides, medicines, materials, etc., especially in the field of medicine. Chinese medicine intermediates. At present, the reported synthetic method is usually using m-nitrobenzaldehyde as a raw material, which first generates m-aminobenzaldehyde through reduction, then synthesizes m-hydroxybenzaldehyde through diazotization and hydrolysis, and then reacts with piperidine to obtain 3-( 1-piperidinylmethyl)phenol. Due to the diazotization reaction involved, there is a certain risk of operation, and the three wastes are produced in a large amount, the yield is low, and the cost is high. Invention content: [0003] The technical problem to be...

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): C07D295/096
CPCC07D295/096
Inventor 董来山
Owner ANHUI HERYI CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap