Preparation method for vinpocetine

A technology of vinpocetine and vincamine, applied in the field of preparation of vinpocetine, which can solve the problems of complicated and difficult operation process and high reaction temperature, and achieve the effects of short process flow, good product quality and low preparation cost

Inactive Publication Date: 2014-03-26
HUNAN KEYUAN BIO PRODS
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Chen Rongrong, Pu Hanlin and others also used this method to synthesize Vinpocetine in "Semi-synthetic Process of Vinpocetine" ("Journal of Jinan University (Natural Science and Medicine Edition)" 2012 Issue 01), but the results were not ideal
[0008] Chinese patent application 201210151559.5 discloses a synthetic method of vinpocetine, which uses methanesulfonyl chloride to carry out mesylation and dehydroxylation, and then uses sodium ethoxide to carry out transesterification in ethanol solution, but it is found that the methyl exchange is difficult, and the reaction The temperature is high, and the time requirement is very long, so the reaction cannot be completed
[0009] Chinese patent application 201210388713.0 discloses a semi-synthetic method of vinpocetine, which uses an acid as a solvent to carry out hi

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

[0027] (1) In a 500ml three-neck flask, add 100g (0.28mol) of raw material vincamine, 250ml of triethyl orthoformate and 20g of rhodium acetate, replace with nitrogen for 3 times, slowly heat to 80°C, and let it react at 80°C After 8 hours, TLC was analyzed. After the reaction was completed, it was naturally cooled to 2° C., and then saturated sodium bicarbonate solution was added dropwise. When the yellow solid gradually precipitated and the pH of the reaction solution was 8, the dripping of saturated sodium bicarbonate solution was stopped. After stirring for 45 minutes, filter, the filter cake was washed with ice purified water until neutral, and dried in vacuum at a drying temperature of 40°C for 12 hours to obtain 96 g of yellow vinpocetine crude product;

[0028] (2) Put the yellow vinpocetine crude product obtained in step (1) into a 500ml three-neck bottle, pour 250ml of ethanol, add 10g of activated carbon, heat to 80°C, keep it warm for 1.5 hours, then filter while it...

Embodiment 2

[0031] In a 500ml three-necked flask, add 100g (0.28mol) of raw material vincamine, then add 250ml of triethyl orthoacetate and 20g of palladium acetate, replace with nitrogen for 3 times, then slowly heat to 80°C, let it react at 80°C for 8 hours Above, TLC is analyzed, after the reaction is completed, naturally cool to 0-5 ° C, dropwise add saturated sodium bicarbonate solution, a yellow solid gradually precipitates, when the pH of the reaction solution=8, stop adding dropwise saturated sodium bicarbonate solution, After stirring for 45 minutes, it was filtered, and the filter cake was washed with ice-purified water to neutrality, and then vacuum-dried at a drying temperature of 40° C. for 12 hours to obtain 93 g of yellow vinpocetine crude product.

[0032] Put the crude product into a 500ml three-neck bottle, pour 250ml of ethanol, add 10g of activated carbon, heat to 80°C, keep it warm for 1.5 hours, filter while it is hot, and cool the filtrate to room temperature natural...

Embodiment 3

[0035] In a clean 500ml three-neck bottle, add 100g of raw material vincamine (0.28mol), add 250ml of triethyl orthoacetate and 20g of cuprous chloride, replace with nitrogen for 3 times, slowly heat to 80°C, and let it ℃ reaction for more than 8 hours, TLC analysis, after the reaction, naturally cooled to 1 ℃, slowly dropwise added saturated sodium bicarbonate solution, yellow solid gradually precipitated, when the pH of the reaction solution = 8, stop dripping saturated sodium bicarbonate solution , stirred for 45 minutes, filtered, the filter cake was washed with ice purified water until neutral, dried in vacuo at a drying temperature of 40° C., and dried for 12 hours to obtain 87 g of yellow vinpocetine crude product.

[0036] Put the above crude product into a 500ml three-necked bottle, pour 250ml of ethanol, add 10g of activated carbon, heat to 80°C, keep warm for 1.5 hours, filter while it is hot, and cool the filtrate to room temperature naturally, then place it in a re...

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 provides a preparation method for vinpocetine. The method comprises the following steps: with vincamine as a raw material and triethyl formate as an esterification reagent, subjecting vincamine and triethyl formate to a one-step reaction under the action of Lewis acid so as to obtain a crude vinpocetine product; and then carrying out washing with alkali lye, decoloring in alcohol and recrystallization so as to prepare a refined vinpocetine product. Compared with the prior art, the preparation method provided by the invention has the advantages of short process flow, simple operation and suitability for industrial production, and the prepared refined vinpocetine product has yield of more than 89%, a melting point of 148 to 151 DEG C, HPLC of greater than 99%, a whitish color, good quality and low preparation cost.

Description

technical field [0001] The invention relates to a preparation method of vinpocetine. Background technique [0002] Vinpocetine is an ivory amine, its English name: Vinpocetine, chemical name: ethyl (13as, 13bs)-13a ethyl-2, 3, 5, 6-13a, 13b hexahydro 1H-indole [3,2,1-de]pyridine [3,2,1 primer [1,5] naphthalene 12-carboxylic acid, the structural formula is as follows: [0003] [0004] Vinpocetine is a cerebral vasodilator, which can inhibit the activity of phosphodiesterase, increase the effect of c-GMP, the messenger of vascular smooth muscle relaxation, and selectively increase cerebral blood flow. In addition, it can also inhibit platelet aggregation, reduce human blood viscosity, enhance Red blood cell deformability, improve blood flow and microcirculation, promote brain tissue uptake of glucose, increase brain oxygen consumption, improve brain metabolism. [0005] There are mainly three kinds of synthetic methods of existing vinpocetine: one is to extract from t...

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): C07D461/00
CPCC07D461/00
Inventor 杨昌勇刘志强
Owner HUNAN KEYUAN BIO PRODS
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