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

Synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol

A technology of aminophenyl and synthesis method, applied in the field of synthesis of -2-[[[2-ethyl]amino]methyl]benzyl alcohol, which can solve human health hazards, cost of dangerous processing, and yield of benzyl alcohol Low-level problems, to achieve the effect of good market competitiveness, good quality, and high product yield

Active Publication Date: 2020-04-14
SUZHOU UUGENE BIOPHARMA
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol yield that this method prepares is lower, and in reaction step, adopts borane dimethyl sulfide And high temperature and high pressure, among which borane dimethyl sulfide is harmful to human health, high temperature and high pressure is not only dangerous but also the cost of processing will be high

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 (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol
  • Synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol
  • Synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: At room temperature, 300 ml of methanol, 137 grams of R-2 (aminomethyl) benzyl alcohol, 155 g of 4-(2 chloroethyl) aniline and 111 g of triethylamine were added to the reaction flask, and the mixture was heated to 60-65°C, stirred and refluxed for 8 hours, pumped the reaction solution into 500g of water while it was hot, cooled to 10-15°C, and filtered to obtain 250g of off-white solid (1R)-2-[[[2-(4-Amino Phenyl) ethyl] amino] methyl] benzyl alcohol, yield 97.6%, purity 99.9%.

Embodiment 2

[0031] Example 2: At room temperature, 300 ml of methanol, 137 grams of R-2 (aminomethyl) benzyl alcohol, 155 g of 4-(2 chloroethyl) aniline and 122 g of triethylamine were added to the reaction flask, and the mixture was heated to 60-65°C, stirred and refluxed for 8 hours, pumped the reaction solution into 500g of water while it was hot, cooled to 10-15°C, filtered to obtain 230g of off-white solid (1R)-2-[[[2-(4-Amino Phenyl) ethyl] amino] methyl] benzyl alcohol, yield 89.8%, purity 97.9%.

Embodiment 3

[0032] Example 3: At room temperature, 300 ml of methanol, 137 grams of R-2 (aminomethyl) benzyl alcohol, 155 g of 4-(2 chloroethyl) aniline and 122 g of triethylamine were added to the reaction flask, and the mixture was heated to 30-35°C, stirred for 8 hours, pumped the reaction solution into 500g of water while it was hot, cooled to 10-15°C, and filtered to obtain 170g of off-white solid (1R)-2-[[[2-(4-Aminobenzene Base) ethyl] amino] methyl] benzyl alcohol, yield 66.6%, purity 81.3%.

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

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol, which comprises the following processing steps: S1, adding R-2 (aminomethyl) benzyl alcohol, 4-(2-chloroethyl) aniline and triethylamine into a solvent at room temperature, and mixing; S2, after heating to 60-65 DEG C, stirring and refluxing for 1-48h; S3, pumping an obtained reaction liquid into water while the reaction liquid is hot; cooling and filtering to obtain a white solid (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol; wherein the molar ratio of R-2 (aminomethyl) benzyl alcohol to 4-(2-chloroethyl) aniline in the step S1 is 1: (1-20), the solubility of 4-(2-chloroethyl) aniline in the solvent in the step S1 is 40%-60%, and the use amount of 4-(2-chloroethyl) aniline is 1-1.5 times of the mass amount of R-2 (aminomethyl) benzyl alcohol. The method has the advantages of mild reaction, simple operation, and green and environment-friendly reaction process; no irritant organic solvent is adopted; dangerous borane dimethyl sulfide is not adopted; high temperature and high pressure are not adopted; and clean production is realized.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of (1R)-2-[[[2-(4-aminophenyl)ethyl]amino]methyl]benzyl alcohol. Background technique [0002] Mirabegron is used to treat overactive bladder in adults. The clinical trial data show that compared with the existing clinical treatment of adults with overactive bladder, mirabegron has the characteristics of rapid onset of action, good tolerance, no sexual dysfunction for patients, and small adverse reactions. Its chemical name is 2-amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide, and its chemical formula is : [0003] [0004] And (1R)-2-[[[2-(4-aminophenyl)ethyl]amino]methyl]benzyl alcohol is an important intermediate in the synthesis of mirabegron. In the prior art, there are patent applications for the synthesis of (1R)-2-[[[2-(4-aminophenyl)ethyl]amino]methyl]benzyl alcohol (publication number: ...

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): C07C213/08C07C215/30
CPCC07C213/08C07B2200/07C07C215/30
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE 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