Synthesis method for compound tulobuterol

A technology of tulobuterol and a synthesis method, which is applied in the field of drug synthesis, can solve the problems of hidden safety hazards and high cost, and achieve the effects of improving production efficiency, less side reactions, and mild reaction conditions

Active Publication Date: 2016-03-30
SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0012] The present invention aims to solve the technical problems of potential safety hazards and high cost in existing methods, and provides a synthetic method of tulobuterol with simple process, safe and easy-to-obtain raw materials, safe operation and high yield, suitable for industrial production

Method used

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  • Synthesis method for compound tulobuterol
  • Synthesis method for compound tulobuterol
  • Synthesis method for compound tulobuterol

Examples

Experimental program
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Effect test

Embodiment 12

[0050] The preparation of embodiment 12-chlorostyrene

[0051]78.3g (0.5mol) of 1-(2-chlorophenyl)-1-ethanol, 40.8g potassium bisulfate (0.3mol) and 5.5g hydroquinone (0.05mol) were added in a 500ml single-necked bottle, and then React at 190-195°C for 3 hours. After cooling down to room temperature, slowly pour the reaction system into 300ml of diethyl ether under stirring, spin the diethyl ether to dryness, add 200ml of dichloromethane and 100ml of water, stir well, separate the water layer, and wash the organic layer 3 times with saturated brine (50ml × 3), after drying, filtering and concentrating over anhydrous sodium sulfate, 61.2 g of 2-chlorostyrene was obtained as a colorless oil, with a yield of 88%.

Embodiment 22

[0052] The preparation of embodiment 22-chlorostyrene

[0053] 78.3g (0.5mol) of 1-(2-chlorophenyl)-1-ethanol, 54.5g potassium bisulfate (0.4mol) and 11.0g hydroquinone (0.1mol) were added in a 500ml single-necked bottle, and then React at 200-205°C for 3 hours. The aftertreatment method was the same as in Example 1 to obtain 62.6 g of the product, with a yield of 90%.

Embodiment 32

[0054] The preparation of embodiment 32-chlorostyrene

[0055] 78.3g (0.5mol) of 1-(2-chlorophenyl)-1-ethanol, 47.7g potassium bisulfate (0.35mol) and 8.3g hydroquinone (0.075mol) were added in a 500ml single-necked bottle, and then React at 210-215°C for 3 hours. The post-treatment method was the same as in Example 1 to obtain 58.4 g of the product, with a yield of 84%.

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Abstract

The invention relates to a synthesis method for compound tulobuterol. The technical problems that potential safety hazards exist in an existing method, and cost is high are solved. The method includes the following steps of a, an olefination reaction, wherein 1-(2-chlorphenyl)-1-ethyl alcohol serves as an initial raw material, and in the presence of a catalyst and acid, a heating reaction is conducted to generate 2-chloro-styrene; b, a cyclization reaction, wherein 2-chloro-styrene serves as a raw material, and in the presence of alkali and an oxidizing agent, an epoxidation reaction is conducted to obtain 2-(2-chlorphenyl) ethylene oxide; c, a ring-opening reaction, wherein 2-(2-chlorphenyl) ethylene oxide serves as a raw material and reacts with tert-butylamine to obtain compound 1-(2-chlorphenyl)-2-tert-butylamino ethanol. The synthesis method can be used for preparing tulobuterol.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for synthesizing the compound tulobuterol Background technique [0002] Tulobuterol, whose chemical name is 1-(2-chlorophenyl)-2-tert-butylaminoethanol, has the following chemical structure: [0003] [0004] Tulobuterol can selectively excite beta 2 -receptor, has a powerful and long-lasting dilating effect on bronchial smooth muscle. It is used to relieve symptoms such as dyspnea caused by bronchial asthma, chronic bronchitis, asthmatic bronchitis, emphysema, sand lung, pneumoconiosis and other respiratory obstructive diseases. [0005] The drug was first developed by Tanabe Pharmaceutical Co., Ltd. (Japan) in the form of its hydrochloride and was first listed in Japan in 1981. Its original research and synthesis method is as follows: from o-chloroacetophenone (2) after bromine bromination Obtain α-bromoacetophenone (3), then use potassium borohydride reduction to o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/30C07C209/00
CPCC07C17/35C07C209/00C07D301/14C07D303/08C07C25/02C07C215/30
Inventor 景亚军何淑旺郭伟
Owner SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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