Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

3-chloro-4-methoxy benzyl amine synthetic method

A technology of methoxybenzylamine and a synthesis method, which is applied in the synthesis field of 3-chloro-4-methoxybenzylamine, can solve the problems of harsh reaction conditions, unfavorable industrialization, and high equipment requirements, and achieves mild reaction conditions and healthy Low hazard and low equipment requirements

Inactive Publication Date: 2016-06-29
重庆瑞泊莱医药科技有限公司
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction temperature of this route is relatively high, the requirements for reaction equipment are very high, and the yield is not high, which is not conducive to industrial production
[0007] In summary, the process for preparing 3-chloro-4-methoxybenzylamine in the prior art either requires relatively high requirements for operators and poses a greater threat to the health of operators; or the yield is low, which is not conducive to industrialization; Either the reaction conditions are harsh and require high equipment, which is not conducive to industrial production

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
  • 3-chloro-4-methoxy benzyl amine synthetic method
  • 3-chloro-4-methoxy benzyl amine synthetic method
  • 3-chloro-4-methoxy benzyl amine synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 compound I3-chloro-4-methoxybenzyl chloride

[0027] Add 800ml of dichloromethane, 138g of 3-chloro-4-methoxybenzyl alcohol and 5ml of DMF into a 2L three-necked flask, and add 96g of thionyl chloride dropwise under stirring. After the dropping, the temperature was slowly raised to reflux until HPLC showed that 3-chloro-4-methoxybenzyl alcohol was less than 0.5%. After cooling down to below room temperature, 800ml of saturated sodium bicarbonate solution was slowly added, and the mixture was stirred for 10min to separate the layers. The aqueous layer was extracted with dichloromethane, the organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and rotary evaporated in a water bath at 35°C to obtain 144g of 3-chloro-4-methoxybenzyl chloride with a yield of 94.3%, [M+H] + =191.

Embodiment 2

[0028] The synthesis of embodiment 2 compound II

[0029] Add 500ml of n-butanol and 93g of urotropine into a 1L three-necked flask, and add 114g of 3-chloro-4-methoxybenzyl chloride dropwise at a controlled temperature of 20-30°C. After dropping, the temperature was slowly raised to reflux for 2 hours, and the temperature was lowered to 20°C to obtain compound II, which was directly put into the next reaction without separation.

Embodiment 33

[0030] The synthesis of embodiment 33-chloro-4-methoxybenzylamine

[0031] 350 g of concentrated hydrochloric acid was added dropwise to Example 2, and the temperature was slowly raised to 50° C. for 1 h after the drop was completed. Cool down to 20°C, filter, adjust the filtrate to pH 13 with sodium hydroxide, and rectify under reduced pressure to collect fractions at 110-115°C (1mmHg) to obtain 81g of colorless oily 3-chloro-4-methoxybenzylamine , yield 80%. [M+H] + =172, 1 HNMR (DMSO-D 6 ): 3.86 (3H, s), 3.94 (2H, s), 7.19 (1H, d), 7.31 (1H, dd), 7.61 (1H, d,), δ8.40 (2H, brs).

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 present invention provides a 3-chloro-4-methoxy benzyl amine synthetic method which is as follows: first chlorination of 3-chloro-4-methoxy benzyl alcohol as a starting material, then formation of a quaternary ammonium salt with urotropin, and acid hydrolysis of the quaternary ammonium salt. The 3-chloro-4-methoxy benzyl amine synthetic method is simple and convenient in operation, product purity is high, and the 3-chloro-4-methoxy benzyl amine synthetic method overcomes the deficiencies of the prior art, and is suitable for large-scale production.

Description

Technical field: [0001] The invention relates to 3-chloro-4-methoxybenzylamine, in particular to a synthesis method of 3-chloro-4-methoxybenzylamine. Background technique: [0002] 3-Chloro-4-methoxybenzylamine, CAS No. 247569-42-2, is an important intermediate in the synthesis of the ED drug avanafil. The structure of 3-chloro-4-methoxybenzylamine is as follows: [0003] [0004] At present, there are mainly two kinds of synthetic methods about 3-chloro-4-methoxybenzylamine: [0005] The first one, document JournalofMedicinalChemistry; vol.31; nb.10; (1988); p.1941-1946 discloses using p-methoxybenzylamine as raw material, acetic acid as reaction solvent, and chlorination with chlorine gas. This route adopts chlorine as a raw material, and in industrial production, the operation and safety requirements of operators are relatively high, and the yield of 3-chloro-4-methoxybenzylamine is low. [0006] The second one, the document JournalofMedicinalChemistry; vol.41; nb.18...

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): C07C217/58C07C213/02
Inventor 李伟陈琳高河勇冉勇
Owner 重庆瑞泊莱医药科技有限公司
Features
  • Generate Ideas
  • 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