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Method for producing amine series and quaternary ammonium salts with adamantane framework

A manufacturing method, adamantane technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds from amines, etc., can solve the problem of slow reaction speed, difficult to purify, unable to obtain the target product with high purity and high yield, etc. problem to achieve high yields

Inactive Publication Date: 2011-03-30
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction speed of this method is slow, and the reaction takes a long time
In addition, since the raw materials cannot be completely reacted, it is difficult to purify, and the target product cannot be obtained with high purity and high yield.

Method used

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  • Method for producing amine series and quaternary ammonium salts with adamantane framework
  • Method for producing amine series and quaternary ammonium salts with adamantane framework
  • Method for producing amine series and quaternary ammonium salts with adamantane framework

Examples

Experimental program
Comparison scheme
Effect test

manufacture example 1

[0141] [Manufacturing Example 1]: Steps 1 and 2

[0142] 100 mL (1937 mmol) of 25 mass % oleum was placed in a 300 mL four-necked flask, 8 g (195 mmol) of acetonitrile and 20 g (147 mmol) of adamantane were added, and the mixture was reacted at a reaction temperature of 25° C. for 3 hours. In addition, the molar ratio of oleum to the raw material adamantane was 13.2 (=1937 / 147).

[0143] Next, the reaction liquid was added dropwise to 300 g of water at 5° C. placed in a 1 L four-necked flask. At the end of the dropwise addition, the temperature of the liquid mixture of water and the reaction liquid was 10°C. After completion of the dropwise addition, stirring was carried out at 10° C. for 30 minutes to complete the hydrolysis, and the precipitated crystals were filtered, washed with water, and dried to obtain 27.5 g of crystals.

[0144] According to gas chromatography analysis, the crystals were N-(1-adamantyl)acetamide with a GC purity of 98%, and the yield was 97 mol%.

manufacture example 2

[0145] [Manufacturing Example 2]: Steps 1 and 2

[0146] Except having changed the amount of acetonitrile to 12 g, the same operation as in Production Example 1 was performed. As a result, 27.8 g of N-(1-adamantyl)acetamide was obtained (98 mol% yield, 98% GC purity).

manufacture example 3

[0147] [Manufacturing Example 3]: Steps 1 and 2

[0148] Except having changed the reaction temperature from 25 degreeC to 40 degreeC, the same operation as manufacture example 1 was performed. As a result, 25.5 g of N-(1-adamantyl)acetamide was obtained (yield 90 mol%, GC purity 95%).

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Abstract

The present invention provides a method for producing amine series with an adamantane framework, including the following steps: step 1: reacting adamantane series in a mixed liquid containing oleum and organic nitrile compounds; step 2: performing hydrolyzing treatment to a reaction liquid obtained in the step 1 to form acidamide series with the adamantane framework; step 3: performing alkali treatment to the acidamide series obtained in the step 2 to form the amine series with the adamantane framework. A method for producing quaternary ammonium salts with the adamantane framework in sequence includes the following steps: step A: reacting the amine series with the adamantane framework dissolved in a dissolvant a with aminic acid and methylene oxide or paraformaldehyde, to form dimethylamine series with the adamantane framework; step B: dissolving the dimethylamine series with the adamantane framework obtained in the step A in a dissolvant b to react with halomethane so as to form quaternary ammonium salt halogenide with the adamantane framework; step C: performing ion exchange to the quaternary ammonium salt halogenide with the adamantane framework to form quaternary ammonium salt hydroxides with the adamantane framework.

Description

technical field [0001] The present invention relates to a method for producing amines and quaternary ammonium salts with an adamantane skeleton. In detail, it relates to a method for producing amines having an adamantane skeleton, and using the amines obtained by the production method, high-purity, high-yield, and simple production of quaternary ammonium halides and quaternary ammonium salts having an adamantane skeleton Hydroxide method. Background technique [0002] Aminoadamantanes, such as 1-aminoadamantane, in which amino groups are bonded to the adamantane skeleton, are widely used in pharmaceutical intermediates, raw materials for photoresist monomers, coatings, adhesives (adhesives), It is an industrially important compound for applications such as raw materials for materials such as adhesives (adhesives), films, and adsorbents. In particular, 1-aminoadamantane hydrochloride (amantadine hydrochloride) is a very important compound as an antiviral agent for influenza...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/62C07C211/38C07C209/12C07C211/62C07C209/68
Inventor 小岛明雄伊藤克树河野直弥
Owner IDEMITSU KOSAN CO LTD
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