Method for synthesizing 2-(1-imidazol)ethylamine

A synthesis method and imidazole-based technology are applied in the field of preparation of fine chemicals, can solve the problems of expensive 2-ethyl-2-oxazoline and difficult to obtain propionamide, and achieve high total yield, mild conditions and convenience Effects of manipulation and control

Inactive Publication Date: 2010-12-08
HEFEI UNIV OF TECH
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In 2006, Popkov S et al. (Russ.Chem.Bull., 2006, 55(10): 1848-1551) used -(2-(1H-imidazol-1-yl)ethyl)propionamide as raw material, hydrolyzed with hydrochloric acid to obtain 2-(1-imidazol-1-yl)ethylamine, the yield is 52%, but the raw material N-(2-(1H-imidazol-1-yl)ethyl)propionamide is not easy to obtain
[0006] In 2006, Popkov S et al. (Russ.Chem.Bull., 2006, 55(10): 1848-1551) used 2-ethyl-2-oxazoline as raw material in SnCl 2 Preparation of 2-(1-imidazolyl)ethylamine as a catalyst, although the yield of this method is 87%, but the raw material 2-ethyl-2-oxazoline is expensive

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
  • Method for synthesizing 2-(1-imidazol)ethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1), the preparation of intermediate (I): add imidazole (4.1g, 60mmol), TEA (1.0ml, 7.2mmol), methanol (60ml) successively in 150ml there-necked flask, slowly add ethyl acrylate (7.7ml , 72mmol), stirred, reacted at 50°C for 5h, column chromatography (CH 2 Cl 2 :CH 3 OH=40:1) to isolate a pale yellow liquid compound (9.4 g) with a yield of 94.8%. 1 HNMR (Cl 3 CD-d 6 )δ: 7.50(s, 1H), 7.04(s, 1H), 6.94(s, 1H), 4.26(t, 2H), 4.13(q, 2H), 2.77(t, 2H), 1.24(t, 3H ).

[0018] (2), the preparation of intermediate (II): 80% hydrazine hydrate (7.5ml, 150mmol), ethanol (30ml), slowly drop the mixture of ethanol (10ml) and intermediate (I) (8.40g, 50mmol), The temperature was not higher than 40°C. After stirring for about 30 minutes, the temperature was raised to reflux for 8 hours. Column chromatography (CH 2 Cl 2 :CH 3 OH=20:3) to isolate yellow compound 2 (7.26g), yield 94.3%. 1 HNMR (Cl 3 CD-d 6 )δ: 8.41(s, 1H), 7.52(s, 1H), 7.04(s, 1H), 6.91(s, 1H), 4.32(t, 2H), 3....

example 2

[0021] Intermediate (I) was prepared according to the method of Example 1, using acetonitrile as solvent, and the rest of the operations were the same.

example 3

[0023] Intermediate (I) was prepared according to the method of Example 1, THF was used as solvent, and the rest of the operations were the same.

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 provides a method for synthesizing 2-(1-imidazol)ethylamine, which uses imidazole and ethyl acrylate as raw material, and includes steps of preparing intermediate (1) ethyl 2-(1-imidazol)propionate from the raw material through Michel addition reaction; preparing intermediate (2) 2-(1-imidazol)propionohydrazide from the intermediate (1) through hydrazinolysis reaction; and obtainingthe object product 2-(1-imidazol)ethylamine from the intermediate (2) through Curtius rearrangement reaction. The invention has total yield of 72% by imidazole, stable reaction, mild condition, and convenient operation and control.

Description

1. Technical field [0001] The invention relates to a preparation method of fine chemicals, in particular to a preparation method of pharmaceutical intermediates, in particular to a synthesis method of 2-(1-imidazolyl)ethylamine as a structural fragment of various medicines. 2. Background technology: [0002] 2-(1-imidazolyl)ethylamine is a structural fragment used in various drugs, such as a structural fragment of N-alkylsulfonamides that inhibit γ-secretase (Carl P. Bergstrom et al., Bioorg. Med.Chem.Lett., 2008, 18 (2): 464-468), structural fragments of nitrogen-containing fused heterocycles with various pharmaceutical activities (Henning Priepke et al., US 7429597), which have the effect of treating malaria Structural fragments of Farnesyl protein transferase inhibitors (William T. Windsor et al., US 6645966) and the like. At present, there are four synthetic methods of this compound, but there are disadvantages such as high cost and low overall yield. [0003] In 1977,...

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 Patents(China)
IPC IPC(8): C07D233/61
Inventor 姚日生江来恩邓胜松钱琴余三喜崔玉杰
Owner HEFEI UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap