Synthesis of 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane

A technology of benzylpiperidine and diazaspiro, which is applied in the field of medicine and can solve the problems of high price, low reaction yield, and difficulty in purification, etc.

Inactive Publication Date: 2012-10-17
CGENETECH (SUZHOU CHINA) CO LTD
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Problems solved by technology

[0005] The present invention aims at the shortcomings of 2-(1-benzylpiperidine)-2,8-diazaspiro[4,5]decane in the past that the synthetic method is expensive, the reaction yield is low, and it is not easy to purify. The route of taking ethyl piperidine-4 carboxylate as a raw material through protection, docking with ethyl bromoacetate, ring-closing with 1-benzylpiperidine-4-ammonia, deprotection, and reduction with lithium tetrahydrogen to obtain the final product, The whole process is easy to operate, the product is easy to purify, and the cost of raw materials is greatly reduced

Method used

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  • Synthesis of 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane
  • Synthesis of 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane

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Embodiment Construction

[0011] Preparation of compound (2):

[0012] Starting material (1) 314 grams (2 moles) was dissolved in 2.2 liters of dichloromethane, 202 grams (2 moles) of triethylamine was added, and 536 grams (2 moles) of di-tert-dicarbonate were added in batches under ice-water cooling Butyl ester, stirred at room temperature overnight after the addition, the reaction solution was poured into 1 liter of ice water, extracted in layers, washed with saturated brine (500 ml), dried over anhydrous sodium sulfate, filtered, spin-dried, and recrystallized from ethanol to obtain 479 grams of a white solid (Yield 93%).

[0013] Preparation of compound (3):

[0014] Dissolve 386 grams (1.5 moles) of compound (2) in 3 liters of anhydrous tetrahydrofuran, cool to minus 78 degrees, add dropwise 1.8 liters of 1N LDA / tetrahydrofuran solution prepared in advance, and use it for about 2 hours. After dripping, keep warm for reaction After 2 hours (minus 78 degrees), add 301 grams (1.8 moles) of ethyl br...

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Abstract

The invention discloses synthesis of 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane. Directed at the shortages of expensiveness, low reaction yield, and difficult purification in previous synthesis methods of 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane, the invention provides the following synthesis route of: taking piperidine-4 carboxylic acid ethyl ester as the raw material and conducting protection on it, then bringing the protected raw material into butt joint with ethyl bromoacetate, and carrying out ring closing with 1-benzylpiperidine-4-ammonia, performing deprotection, and implementing reduction with tetrahydro lithium aluminum, thus obtaining the 2-(1-benzylpiperidine)-2, 8-diazaspiro[4, 5]decane. According to the invention, the whole process is easy to operate, the product is easy to purify, and the raw material cost is greatly reduced.

Description

technical field [0001] The invention relates to the synthesis of 2-(1-benzylpiperidine)-2,8-diazaspiro[4,5]decane, belonging to the technical fields of medicine and chemical industry. Background technique [0002] 2-(1-benzylpiperidine)-2,8-diazaspiro[4,5]decane spiro products are important chemical products, widely used in the fields of medicine and pesticides, especially in the screening of new drug lead compounds On the one hand, most of the synthetic routes of analogues reported at present are to reduce the benzylpiperidone to alcohol and then turn the hydroxyl group into an active leaving group, and then combine with 2,8-diazaspiro[4,5]decane -8-carboxylic acid tert-butyl ester substitution, deprotection to obtain the product, the specific route is as follows: [0003] [0004] The above route has disadvantages such as high price of tert-butyl 2,8-diazaspiro[4,5]decane-8-carboxylate, low reaction yield and difficult purification. Contents of the invention [0005...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
Inventor 张福治丁炬平张仁延余强
Owner CGENETECH (SUZHOU CHINA) CO LTD
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