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

Synthesis method for N-methoxymethyl-N-(trimethylsilyl methyl)benzylamine

A technology of trimethylsilylmethylbenzylamine and trimethylchloromethylsilane, applied in the field of synthesis of N-methoxymethyl-N-benzylamine

Inactive Publication Date: 2015-03-25
WUXI QIANHAO BIOPHARMA
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no report on the relevant patented technology of this reagent in China

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 for N-methoxymethyl-N-(trimethylsilyl methyl)benzylamine
  • Synthesis method for N-methoxymethyl-N-(trimethylsilyl methyl)benzylamine

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0014] Weighed trimethylchloromethylsilane (245.4 g, 2 mol) into a three-necked flask, evacuated it with nitrogen protection, and heated it up. When the temperature rises to 85 °C, start to add BnNH slowly 2 (556.4g, 5.2mol), the system was heated up slowly, the reaction temperature was controlled at 120°C, and the BnNH 2 After the dropwise addition, continue to maintain the system at 120°C for about 12 hours, and stop heating after the reaction is complete. After the system cools down to room temperature, remove the solids by filtration, soak and filter the filter cake with petroleum ether (150ml×2) until there is no product residue, collect the filter cake (benzylamine hydrochloride); the washings and filtrates are combined (about 1000ml) , washed three to four times with about 4L of water; the organic phase was mixed and dried with anhydrous potassium carbonate and anhydrous sodium sulfate, and the organic phase was distilled off under reduced pressure at 100°C-200°C, and ...

example 2

[0016] Weighed trimethylchloromethylsilane (245.4 g, 2 mol) into a three-necked flask, evacuated it with nitrogen protection, and heated it up. When the temperature rises to 85 °C, start to add BnNH slowly 2 (428g, 4mol), the system was heated up slowly, the reaction temperature was controlled at 100°C, and the BnNH 2 After the dropwise addition, continue to maintain the system at 200°C for about 5 hours, and stop heating after the reaction is complete. After the system cools down to room temperature, remove the solids by filtration, soak and filter the filter cake with petroleum ether (150ml×2) until there is no product residue, collect the filter cake (benzylamine hydrochloride); the washings and filtrates are combined (about 1000ml) , washed three to four times with about 4L of water; the organic phase was mixed and dried with anhydrous potassium carbonate and anhydrous sodium sulfate, and the organic phase was distilled off under reduced pressure at 100°C-200°C, and the c...

example 3

[0018] Weigh formaldehyde aqueous solution (37%) (198.7g, 2.52mol) in a 250ml three-necked flask, evacuate and ventilate nitrogen protection, cool to 0°C in an ice-salt bath, and then add trimethylsilylmethylbenzylamine (331.2g, 1.72mol) was added dropwise into a three-necked flask, the temperature was controlled at 0°C, and the reaction was stirred for 1 h after the injection was completed, then anhydrous potassium carbonate (187.4g, 1.39mol) was added in batches at -5°C, and methanol (229.2 g, 7.15mol), stop cooling, warm up to room temperature, and stir overnight. After the reaction was completed, the filtrate was allowed to stand and separated into layers, and the upper layer was distilled off under reduced pressure to remove a small amount of methanol, and concentrated to obtain about 364.3 g of crude product N-methoxymethyl-N-(trimethylsilylmethyl)benzylamine. Under reduced pressure distillation, 77-80 degree fractions were collected under 0.5 mm Hg pressure to obtain 30...

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 practical method for synthesis of N-methoxymethyl-N-(trimethylsilyl methyl)benzylamine. The reagent is widely used in synthesis of polysubstituted pyrrolidine compounds and medical intermediates.

Description

technical field [0001] The invention provides a practical synthetic method for preparing N-methoxymethyl-N-(trimethylsilylmethyl)benzylamine, which is widely used in the synthesis of polysubstituted pyrrolidine compounds and pharmaceutical intermediates . Background technique [0002] In recent years, multi-substituted pyrrolidine compounds and pharmaceutical intermediates have attracted widespread attention due to the biopharmaceutical activity of these compounds. Pyrrolidine synthetic building blocks are widely used in many new drug research and development fields, and the market demand is relatively large. At present, there is no efficient method for synthesizing multi-substituted pyrrolidine compounds in the preparation method of pyrrolidine compounds. N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine can form azimine-type ylides under mild conditions, which can undergo 1,3-cycloaddition with substituted alkenes to give Various polysubstituted pyrrolidines. [0003...

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): C07F7/10
Inventor 彭海燕
Owner WUXI QIANHAO BIOPHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com