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Method for synthesizing 2-(1-benzimidazolyl) ethylamine

A benzimidazole-based, synthetic method technology, applied in the field of practical synthesis of 2-ethylamine, can solve the problems of post-processing difficulties, low total yield, inconvenient reaction operation, etc., and achieve reasonable reaction process design and high total yield High, smooth response effect

Inactive Publication Date: 2011-02-16
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to develop a simple and general synthetic method of 2-(1-benzimidazolyl)ethylamine, which mainly solves the problems of inconvenient reaction operation, difficult post-processing, and low total yield in known synthetic methods. question

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] (1), the synthesis of intermediate (I) 2-(1-benzimidazolyl) methyl propionate

[0015]

[0016] Add benzimidazole (5.9g, 50mmol), triethylamine (0.15g, 1.5mmol), methanol (50ml) successively into a 100mL two-necked flask equipped with a reflux condenser and a stirrer, stir to dissolve, and heat up to 40°C. Methyl acrylate (5.2 g, 60 mmol) was added dropwise. The end point of the reaction was monitored by TLC ((developer chloroform:methanol=9:1 / v:v). After the reaction was completed, excess methyl acrylate was distilled off to obtain a white paste solid compound (9.9 g), with a yield of 97%. 1 H NMR (400Hz, CDCl 3 ): δ2.88(t, J=6.4Hz, 2H), 3.67(s, 3H), 4.52(t, J=6.4Hz, 2H), 7.27-7.34(m, 2H), 7.39-7.41(m, 1H), 7.80-7.83(m, 1H), 7.99(s, 1H).

[0017] (2), the synthesis of intermediate (II) 2-(1-benzimidazolyl) propionyl hydrazide

[0018]

[0019] Add 85% hydrazine hydrate (5mL, 100mmol) and methanol (20ml) to a 100mL two-necked flask equipped with a reflux conde...

Embodiment 2

[0024] (1), the synthesis of intermediate (I) 2-(1-benzoimidazolyl) ethyl propionate

[0025]

[0026] Add benzimidazole (5.9g, 50mmol), tetrabutylammonium hydroxide (0.26g, 1.0mmol), ethanol (50ml) successively into a 100mL two-necked flask equipped with a reflux condenser and a stirrer, stir to dissolve, and heat up to 60°C , ethyl acrylate (8.3 g, 75 mmol) was added dropwise. The end point of the reaction was monitored by TLC ((developer chloroform:methanol=9:1 / v:v). After the reaction was completed, excess methyl acrylate was distilled off to obtain a white paste solid compound (10.4 g), with a yield of 95%.

[0027] (2), the synthesis of intermediate (II) 2-(1-benzimidazolyl) propionyl hydrazide

[0028]

[0029] Add 85% hydrazine hydrate (4mL, 80mmol) and ethanol (20ml) into a 100mL two-necked flask equipped with a reflux condenser and a stirrer, and add the intermediate (I) 2-(1-benzimidazolyl) dropwise under stirring. ) Ethyl propionate (8.2g, 40mmol) in ethano...

Embodiment 3

[0033] (1), the synthesis of intermediate (I) 2-(1-benzimidazolyl) methyl propionate

[0034]

[0035] Add benzimidazole (1.2g, 10mmol), triethylamine (0.05g, 0.5mmol) and ethanol (20ml) successively into a 100mL two-necked flask equipped with a reflux condenser and a stirrer, stir to dissolve, and heat up to 40°C. Methyl acrylate (1.1 g, 12 mmol) was added dropwise. The end point of the reaction was monitored by TLC ((developer chloroform:methanol=9:1 / v:v). After the reaction was completed, excess methyl acrylate was distilled off to obtain a white paste solid compound (2.0 g), with a yield of 98%.

[0036] (2), the synthesis of intermediate (II) 2-(1-benzimidazolyl) propionyl hydrazide

[0037]

[0038] Add 85% hydrazine hydrate (1mL, 20mmol) and n-propanol (20ml) in a 100mL two-necked flask equipped with a reflux condenser and a stirrer, and add the mixture containing intermediate (I) 2-(1-benzimidazole) dropwise under stirring. Base) ethyl propionate (2.1 g, 10 mmol)...

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Abstract

The invention discloses a method for synthesizing 2-(1-benzimidazolyl) ethylamine, comprising the following steps of: with a conventional industrial raw material of benzimidazole as an initial raw material, firstly, subjecting the benzimidazole and acrylic resin to a Michael addition reaction to prepare an intermediate of (I) 2-(1-benzimidazolyl) propionic ether; secondly, subjecting the intermediate (I) to a hydrazinolysis reaction to prepare an intermediate (II) 2-(1-benzimidazolyl) propionamide; and finally, subjecting the intermediate (II) to a Kertesz rearrangement reaction to obtain a target object of 2-(1-benzimidazolyl) ethylamine. The synthetic path is shown In the specification. The invention has the advantages of stable reaction, mild conditions and high total yield and is convenient to operate and control.

Description

technical field [0001] The invention relates to a preparation method of fine chemicals, in particular to a practical synthesis method of 2-(1-benzimidazolyl)ethylamine. Background technique [0002] 2-(1-benzimidazolyl) ethylamine is a kind of useful drug intermediate, has the structural fragment (Paul Galatsis et al., Bioorg.Med.Chem.Lett ., 2010, 20:5184-5190), also have structural fragments of sulfa drugs that inhibit γ-secretase (Carl P.Bergstrom et al., Bioorg.Med.Chem.Lett., 2008,18:464- 468), and also a catalyst for synthetic resin (KudoKenji et al., JP 2010215610). There are not many reports about the synthesis method of this compound at present, and the existing synthesis methods have disadvantages such as high cost, uneasy control of reaction conditions, and low overall yield. [0003] In 1957, William B. Wheatley et al. (J.Org.Chem., 1957, 22, 923-925) used benzimidazole as a raw material, first carried out Michael addition reaction with acrylamide, and then obt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/06
Inventor 高国华董智云
Owner EAST CHINA NORMAL UNIV
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