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Preparation method of 5,6-diethyl-2,3-dihydro-1H-indene-2-amine hydrochloride

A technology of amine hydrochloride and diethyl, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of high price and industrial production restrictions, and achieve the effect of low price and easy industrial implementation

Inactive Publication Date: 2015-04-22
湖北万知化工医药股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And raw material 2,3-dihydro-1H-indene-2-amine is rare and expensive commodity on the market, to 5,6-diethyl-2,3-dihydro-1H-indene-2-amine salt There are certain restrictions on the industrial production of acid salts

Method used

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  • Preparation method of 5,6-diethyl-2,3-dihydro-1H-indene-2-amine hydrochloride

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Embodiment 1

[0022] A preparation method of 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride, the steps are as follows:

[0023] (1) Synthesis of compound Ⅰ

[0024] Put 780g of aluminum trichloride and 8L of dichloromethane into a 10L three-necked bottle, cool to -1-1°C, add 600g of 3-chloropropionyl chloride dropwise, react for 30min after the dropwise addition, then add 500g of ethylbenzene dropwise, after the dropwise addition is completed Rise to room temperature (20-25°C) and react for 8 hours, then pour the reactant into 10L 1M hydrochloric acid ice water (hydrochloric acid ice-water mixture) to extract, extract with dichloromethane, wash once with saturated sodium bicarbonate, wash once with water, no Dry over sodium sulfate, spin dry, then freeze and crystallize, and dry to obtain 847g of solid with a melting point of 63-64°C. The product was confirmed by NMR with a yield of 90%.

[0025] (2) Synthesis of compound Ⅱ

[0026] Put 1.5L of 98% concentrated sulfuric acid into ...

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Abstract

The invention belongs to the technical field of synthesis of a medical immediate, and particularly relates to a synthesis method of a key intermediate 5,6-diethyl-2,3-dihydro-1H-indene-2-amine hydrochloride of indacaterol. The method comprises the following steps: by taking ethylbenzene as a raw material, preparing a compound I by propionyl chloride; preparing a compound II from the compound I by cyclization reaction; preparing a compound III by reaction of the compound II and butyl nitrite; preparing a compound IV from the compound III by palladium hydrogen reduction; finally preparing a compound V from the compound IV under protection of trifluoroacetyl; preparing a compound VI from the compound V by amino acetylation reaction; preparing a compound VII from the compound VI by reduction; carrying out deprotection, hydrolysis and acidification on the compound VII, so as to obtain the final product compound VIII, namely the 5,6-diethyl-2,3-dihydro-1H-indene-2-amine hydrochloride. The method disclosed by the invention is simple and convenient to operate, reasonable in reaction flow, low in cost, good in product quality, free of pollution to environment, and applicable to industrial production; the content is greater than 99%.

Description

technical field [0001] The present invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to the synthesis of a key intermediate of indacaterol, 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride method. Background technique [0002] Indacaterol is a new ultra-long-acting β2-receptor agonist developed by Novartis, Switzerland. The drug was approved by the US FDA on July 1, 2011. This medicine is used in the treatment of patients with airflow obstruction in chronic bronchial obstructive disease (COPD), including chronic bronchitis and / or emphysema. 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride is the most critical intermediate of indacaterol, so its market prospect and economic benefits have great potential. [0003] The synthesis method of 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride reported in the literature (such as Organic Process Research & Development 2006,10,135141) is mainly based on 2,3- Dihydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/42C07C209/00C07C209/30
Inventor 鲁东安周叶兵杜小兰刘杰
Owner 湖北万知化工医药股份有限公司
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