Synthesis method of homatropine hydrobromide

A kind of hydrobromide homatropine and synthetic method technology, applied in the direction of organic chemistry, etc., can solve problems such as difficult large-scale industrial production, unstable quality of finished products, mild reaction conditions, etc., to avoid the use of toxic solvent benzene, The effect of low production cost and improved reaction yield

Inactive Publication Date: 2010-02-10
ZHEJIANG UNIV OF TECH
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of this invention is to provide a kind of synthetic method of homatropine hydrobromide, to overcome the reaction condition that exists in the prior art

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
  • Synthesis method of homatropine hydrobromide
  • Synthesis method of homatropine hydrobromide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of compound (III)

[0024] Add 10g of tropinol and 80mL of dichloromethane into a 250mL three-necked flask equipped with mechanical stirring, reflux condenser and thermometer, stir to dissolve, add 17g of O-formylmandeloyl chloride dropwise, and stir at room temperature for 5 hours. After the reaction, the solvent was distilled off under reduced pressure to obtain 20.5 g of crude compound (III).

Embodiment 2

[0025] Embodiment 2: the preparation of compound (III)

[0026] Add 10g of tropinol, 14g of triethylamine, and 80mL of dichloromethane into a 250mL three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a thermometer, stir to dissolve, add 17g of O-formylmandeloyl chloride dropwise, and stir at room temperature for 5 hours Rear. After the reaction was completed, it was washed with water, and the organic layer was separated and concentrated to obtain 20.6 g of crude compound (III).

Embodiment 3

[0027] Embodiment 3: the preparation of compound (III)

[0028] Add 10g of tropinol, 14g of triethylamine, and 80mL of toluene into a 250mL three-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer, stir to dissolve, add 17g of O-formylmandelic acid chloride dropwise, and stir for 8 hours at room temperature. After the reaction was completed, it was washed with water, and the organic layer was separated and concentrated to obtain 21.0 g of crude compound (III).

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 synthesis method of a homatropine hydrobromide shown in a formula (V), comprising the following steps of: tropine shown in a formula (I) and a compound (III) obtained by esterification of O-formyl almond acyl chloride shown in a formula (II); acidic hydrolysis is carried out to the compound (III) to obtain a compound (IV); and the compound (IV) is salified by the hydrobromide to obtain a compound (V). The synthesis method has the beneficial effects of: avoiding the use of benzene as a toxic solvent, having mild reaction condition, simple operation, short production period, high reaction yield and low production cost, being applicable to industrial production and having larger implement value and social and economical benefits.

Description

(1) Technical field [0001] The present invention relates to the synthetic method of drug homatropine hydrobromide (chemical name: α-hydroxy-phenylacetic acid-8-methyl-8-azabicyclo[3.2.1]-3-octyl hydrobromide) . (2) Background technology [0002] Homatropine hydrobromide is a synthetic anticholinergic drug, which has the effect of blocking acetylcholine, causing pupillary sphincter and cycloplegia to cause mydriasis and accommodative paralysis, and is faster and weaker than atropine. A cycloplegic agent indicated for ophthalmic examinations and optometry. There are not many reports on the synthesis method of this compound. There are not many literatures about the synthesis of homatropine hydrobromide. Patents SU199149 and DD11056 report the direct reaction of tropin alcohol and mandelic acid to prepare homatropine. This method uses a more toxic solvent, benzene, as the reaction medium. Not only the environmental pollution is serious, but also the conversion of raw material...

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): C07D451/10
Inventor 张兴贤俞洪正
Owner ZHEJIANG UNIV OF TECH
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