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Synthesis method of 2-(2-methoxyphenoxy)ethylamine

The technology of a methoxyphenoxy group and a synthesis method is applied in the synthesis field of 2-ethylamine, and can solve the problems of long reaction route, high production cost, expensive reaction reagents and the like

Pending Publication Date: 2021-12-31
HANGZHOU GUORUI BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In summary, the existing method for synthesizing 2-(2-methoxyphenoxy)ethylamine also has the disadvantages of long reaction route, cumbersome operation, expensive reaction reagents, harsh process conditions, unfavorable for industrialization, and high production cost

Method used

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  • Synthesis method of 2-(2-methoxyphenoxy)ethylamine
  • Synthesis method of 2-(2-methoxyphenoxy)ethylamine
  • Synthesis method of 2-(2-methoxyphenoxy)ethylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Preparation of 2-(2-methoxyphenoxy)ethylamine:

[0028] Add guaiacol (12.41g, 0.1mol), urea (9.60g, 0.16mol), ethanolamine (9.76g, 0.16mol) and potassium hydroxide (2.80g, 0.05mol) to a 250ml single-necked bottle, and heat at 120°C , program temperature rise to 170°C (10°C every half hour), keep warm for 6h, add ethylenediamine (3.00g, 0.05mol), continue heating at 170°C for 2h, add 50ml water to the reaction product after cooling to dissolve, concentrated Adjust the pH to 2 with hydrochloric acid, filter, add 50 ml of chloroform to the water layer and wash once, adjust the pH to 13 with 20% sodium hydroxide solution, add 50 ml of chloroform for extraction, distill off the chloroform under reduced pressure to obtain 11.4 g of a brownish black liquid, the purity of which is 52.9% by GC , yield 36.1%.

Embodiment 2

[0030] Preparation of 2-(2-methoxyphenoxy)ethylamine:

[0031] Add guaiacol (12.41g, 0.1mol), urea (9.60g, 0.16mol), ethanolamine (9.76g, 0.16mol), potassium hydroxide (0.56g, 0.01mol) to a 250ml single-mouth bottle, add 50ml Dissolve trimethylbenzene, heat at 120°C, program temperature rise to 170°C (10°C per hour), keep warm for 15 hours, add ethylenediamine (3.00g, 0.05mol), heat at 170°C for 2h, add 50ml of water to the reaction product after cooling Dissolve, adjust pH=2 with concentrated hydrochloric acid, filter, add 50ml chloroform to the aqueous layer, wash once, adjust pH=13 with 20% sodium hydroxide solution, add 50ml chloroform for extraction, evaporate chloroform under reduced pressure, and obtain 12.7g brownish black liquid, purity 97.0 %, yield 73.4%.

Embodiment 3

[0033] Preparation of 2-(2-methoxyphenoxy)ethylamine:

[0034] Add 30ml of mesitylene, guaiacol (12.41g, 0.1mol), urea (9.60g, 0.16mol), ethanolamine (9.76g, 0.16mol) and potassium hydroxide (0.56g, 0.01mol) to a 250ml single-necked bottle ), heated at 120°C, programmed to heat up to 170°C (10°C every half hour), keep warm for 20h, add ethylenediamine (3.00g, 0.05mol), heat at 170°C for 2h, add 50ml of water to the reaction product after cooling to dissolve, Concentrated hydrochloric acid to adjust pH=2, filter, add 50ml chloroform to the water layer, wash once, adjust pH=13 with 20% sodium hydroxide solution, add 50ml chloroform for extraction, evaporate chloroform under reduced pressure to obtain 11.6g brownish black liquid, purity 87.3 by GC %, yield 60.1%.

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Abstract

The invention provides a synthesis method of 2-(2-methoxyphenoxy)ethylamine, and belongs to the technical field of organic synthesis. According to the invention, guaiacol, urea and ethanolamine are taken as starting raw materials, and the 2-(2-methoxyphenoxy)ethylamine is synthesized by completing a three-step reaction through a 'one-pot method'. The invention provides a brand new synthesis thought of 2-(2-methoxyphenoxy)ethylamine, innovatively avoids direct use of expensive 2-oxazolidinone, uses urea and ethanolamine to synthesize 2-oxazolidinone, and then directly reacts with guaiacol under the catalysis of alkali to generate 2-(2-methoxyphenoxy)ethylamine.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-(2-methoxyphenoxy)ethylamine. Background technique [0002] 2-(2-methoxyphenoxy)ethylamine is an important intermediate in the synthesis of the β-receptor blocker carvedilol, which is a drug for the treatment of essential hypertension. Used alone or in combination with other antihypertensive drugs, especially thiazide diuretics, carvedilol can also be used in the treatment of symptomatic congestive heart failure to reduce mortality and hospitalization for cardiovascular events and improve patient general condition and slow down disease progression. There are various synthesis methods for 2-(2-methoxyphenoxy)ethylamine in the prior art, but the yield is low and the cost is high. [0003] For example, the patent WO2009128088A2 discloses the preparation method of 2-(2-methoxyphenoxy)ethylamine. First, guaiacol and 1,2-dichloroethane ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/06C07C217/20
CPCC07C213/06C07C217/20
Inventor 陈正树田湘寅王鹏刘国杰
Owner HANGZHOU GUORUI BIO TECH CO LTD
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