Check patentability & draft patents in minutes with Patsnap Eureka AI!

Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate

A synthetic method, the technology of vilazodone, which is applied in the field of synthesis of vilazodone intermediates, can solve the problems of cumbersome post-processing, low yield, long reaction time, etc., shorten the reaction time and increase the product yield , The effect of simplifying the production process

Active Publication Date: 2018-02-09
连云港恒运药业有限公司
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the cyclization process, there are problems such as long reaction time, low yield and cumbersome post-treatment, so it is necessary to seek a synthetic method with easier operation and higher yield

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
  • Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate
  • Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate
  • Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] 19.1 g of 6-nitrocoumarin and 200 ml of chloroform were added to the reaction flask, and 16.7 g of liquid bromine was added dropwise at a temperature of 0-20°C under cooling in an ice-water bath. After the reaction is complete, add 200ml of saturated aqueous sodium carbonate solution, stir, separate layers, separate the organic layer, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 33.0g of 3,4-dibromo-6-nitrochroman-2-one , yield 94%.

Embodiment 2

[0033]

[0034] Add 35.1 g of 3,4-dibromo-6-nitrochroman-2-one prepared according to Example 1 into the reaction flask, add 500 ml of ethanol, and heat to reflux for 1 hour. After the reaction was completed, 25 ml of triethylamine was added, and the mixture was heated to reflux for 8 hours. After the reaction is complete, ethanol is recovered by concentration under reduced pressure. After concentrating to remove most of the ethanol, add 250ml of water, adjust the pH to 6-7 with 0.1mol / L hydrochloric acid, filter, wash the filter cake with water, and dry in vacuo to obtain 5-nitrobenzofuran- 2-carboxylate ethyl ester 21.6g, two-step yield 92%

Embodiment 3

[0036]

[0037] Add 20.0 g of ethyl 5-nitrobenzofuran-2-carboxylate prepared according to Example 2 into the reaction flask, add 300 ml of ethanol, add 2 g of 5% palladium carbon, replace it twice with hydrogen, and control the hydrogen pressure to 0.3 -0.5MPa, 10-30°C hydrogenation reaction for 3 hours, the reaction was completed, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain 17.1 g of ethyl 5-aminobenzofuran-2-carboxylate, with a yield of 98%.

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 relates to a synthetic method for a vilazodone intermediate, i.e., ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate. The key vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate as shown in a formula I is prepared with 6-nitrocoumarin as a starting raw material through addition, ring opening, intramolecular ring closure, nitro reduction, piperazine ring preparation, etc. The synthetic method is simple in synthetic route, high in the yield of target products and suitable for industrial scale-up production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing a vilazodone intermediate. Background technique [0002] Vilazodone hydrochloride (Vilazodone hydrochloride), the chemical name is 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzene Furamide hydrochloride is a new antidepressant drug developed by Clinical Data. In January 2011, the U.S. Food and Drug Administration (FDA) approved vilazodone hydrochloride tablets for the treatment of moderate to severe depressive disorder (MDD) in adults. Compared with existing clinical antidepressants, vilazodone hydrochloride has a rapid onset of action. , high safety, and no side effects of sexual dysfunction for patients. Its chemical structure is as shown in formula (A): [0003] [0004] 5-(1-piperazinyl)-2-benzofuran carboxylic acid ethyl ester is an important intermediate in the synthesis of vilazodone hydrochloride, and the route of vilazodone hydr...

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): C07D307/85
CPCC07D307/85
Inventor 冯芮茂董淑求张庆捷
Owner 连云港恒运药业有限公司
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