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Method for preparing 2-methyl-1-substituted phenyl-2-propyl amine compound

A compound and phenyl technology, applied in the field of pharmaceutical synthesis, can solve problems such as low yield, and achieve the effects of simple operation, cheap and easy-to-obtain raw materials, and improved yield

Inactive Publication Date: 2015-11-25
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The present invention overcomes the shortcoming of low yield in the prior art, and the total yield through the four-step reaction is close to 50%.

Method used

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  • Method for preparing 2-methyl-1-substituted phenyl-2-propyl amine compound
  • Method for preparing 2-methyl-1-substituted phenyl-2-propyl amine compound
  • Method for preparing 2-methyl-1-substituted phenyl-2-propyl amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of 2-methyl-1-(2-methylphenyl)-2-propanamine (5a; R=2-Me)

[0040] Step 1: Preparation of 2-methyl-1-(2-methylphenyl)-2-butyronitrile (2a; R=2-Me)

Embodiment 1

[0041] Example 1: Dissolve diisopropylamine (1.88mL, 13.4mmol, 1.1eq) in 10mL of tetrahydrofuran, ice-bath to -78°C, and 2 Under protection, n-butyllithium (2.8mL, 7.0mmol, 1.1eq) was added dropwise, and after stirring for 30min, light yellow LDA was prepared. Isobutyronitrile (2.39mL, 26.6mmol, 1.1eq) was added dropwise to the reaction, stirred for 1 hour, then 2-methylbenzyl chloride (1.5g, 10.6mmol) was added, and the reaction was stopped after stirring for 25min. Add 10mL of 10% hydrochloric acid and 30ml of water to the mixture to quench the reaction, extract 3 times with 20mL of ethyl acetate, wash 3 times with 15mL of water and 3 times with 15mL of saturated brine, pour the organic phase into Add an appropriate amount of anhydrous sodium sulfate to a clean Erlenmeyer flask and dry it for half an hour. After purification by column chromatography, a pale yellow liquid was obtained with a yield of 98%. 1 HNMR (300MHz, CDCl 3 ): δ7.30-7.16 (m, 4H), 2.88 (s, 2H), 2.38 (s,...

Embodiment 2

[0042] Example 2: Other conditions were the same as Example 1, except that the molar ratio of 2-methylbenzyl chloride to isobutyronitrile was changed to 1:3, and the yield of the obtained product was 95%.

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Abstract

The invention discloses a novel method for synthesizing a 2-methyl-1-substituted phenyl-2-propyl amine compound. The 2-methyl-1-substituted phenyl-2-propyl amine compound can be used for preparing beta2-adrenergic receptor stimulant drugs. Substituted benzyl halide is adopted as a raw material, and reacts with isobutyronitrile under the action of alkali, obtained 2-methyl-1-substituted phenyl-2-butyronitrile is subjected to hydrolysis, a Curtius rearrangement reaction and catalytic hydrogenation, and 2-methyl-1-substituted phenyl-2-propyl amine is generated. The method is easy and convenient to operate, and total yield is obviously improved.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a new synthesis method of 2-methyl-1-substituted phenyl-2-propanamine compounds. Background technique [0002] Bronchial asthma (asthma) and chronic obstructive pulmonary disease (COPD) are common chronic airway inflammatory diseases today, and the global morbidity and mortality are on the rise. workers' attention. beta 2 - Adrenoceptor agonists have been used over the past few decades to treat lung diseases like asthma due to their bronchodilation effect, which rapidly and effectively reduces bronchial smooth muscle tone. Among them, BI-167107 is a long-acting beta2 agonist (long-acting beta2agonists, LABA), which has the effect of causing bronchiectasis, so it is used for the treatment of asthma and chronic obstructive pulmonary disease, and is currently undergoing clinical trials. The structure of BI-167107 and other similar compounds contains a side chain of 2-methy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/62C07C211/27C07C211/29C07C253/30C07C255/33C07C255/35C07C255/37C07C51/08C07C57/30C07C57/58C07C59/64
Inventor 陈新
Owner CHANGZHOU UNIV
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