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Alpha-amino cyclo nitrile compound preparation method

A technology of aminocyclonitrile and compound, which is applied in the field of preparation of organic compounds, can solve problems such as increased organic solvent recovery cost, high price of organic cyanide, difficulty in catalyst recovery, etc., and achieves low cost, low production cost and high yield Effect

Inactive Publication Date: 2012-10-17
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction using the above-mentioned organic cyanide and catalyst must be carried out in an organic solvent, causing certain pollution to the environment, and there are also disadvantages such as expensive organic cyanide, difficulty in catalyst recovery, increased organic solvent recovery cost, and cumbersome operation.

Method used

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  • Alpha-amino cyclo nitrile compound preparation method
  • Alpha-amino cyclo nitrile compound preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 30 grams of cyclohexanone, 0.306 mol of organic amine salt or 25 grams of ammonium bicarbonate into a 500 ml four-neck flask with airtight stirring, a thermometer and a dropping funnel, cool down to 0 ° C, and dropwise add Add 100 grams of sodium cyanide aqueous solution, dropwise in 40 minutes, slowly heat up to 20°C in 30 minutes, keep warm and stir for reaction, use gas chromatography to detect the disappearance of cyclohexanone as the end point of the reaction; after the reaction, extract the reaction solution with ether for 3 times , 150ml each time, combined the organic layers, washed 3 times with 50ml each time, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was rotary distilled to remove the solvent to obtain the product α-aminocyclohexane nitriles. The specific reaction conditions and results are shown in Table 1.

[0020] Table 1 Preparation of α-aminocyclohexane nitrile compounds

[0021]

Embodiment 2

[0023] Add 30 grams of cyclohexanone, 0.306 mol of organic amine salt or 25 grams of ammonium bicarbonate into a 500 ml four-neck flask with airtight stirring, a thermometer and a dropping funnel, cool down to 0 ° C, and dropwise add 133 grams of potassium cyanide aqueous solution was added dropwise in 40 minutes, slowly heated to 25°C in 30 minutes, kept warm and stirred for reaction, and the disappearance of cyclohexanone was detected by gas chromatography as the end point of the reaction; after the reaction, the reaction solution was extracted 3 times with ether , 150ml each time, combined the organic layers, washed 3 times with 50ml each time, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was rotary distilled to remove the solvent to obtain the product α-aminocyclohexane nitriles. The specific reaction conditions and results are shown in Table 2.

[0024] Table 2 Preparation of α-aminocyclohexane nitriles

[0025]

Embodiment 3

[0027] Add 30 grams of cyclohexanone, 0.306 mol of organic amine salt or 25 grams of ammonium bicarbonate, and 27 grams of acetone cyanohydrin into a 500 ml four-neck flask with airtight stirring, thermometer and dropping funnel, cool down to 0 °C, and add saturated carbonic acid dropwise. 220 grams of potassium aqueous solution was added dropwise in 40 minutes, slowly warming up to 30° C. in 30 minutes, insulated and stirred for reaction, and the disappearance of cyclohexanone was detected by gas chromatography as the end point of the reaction; after the reaction was finished, the reaction solution was extracted 3 times with ether, 150ml each time, combined the organic layers, washed 3 times with 50ml each time, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was rotary distilled to remove the solvent to obtain the product α-aminocyclohexane nitrile compound. The specific reaction conditions and results are shown in Table 3.

[0028] Table 3 Prepa...

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Abstract

The invention discloses an alpha-amino cyclo nitrile compound preparation method. Cycloalkanone, organic amine salt or inorganic amine salt, and alkali metal cyanide or acetone cyanohydrin undergo a reaction with stirring in water at the temperature of 20 DEG C to 30 DEG C in the absence of a catalyst to prepare the alpha-amino cyclo nitrile compound. According to the method, the cycloalkanone, the organic amine salt or the inorganic amine salt, and the alkali metal cyanide or the acetone cyanohydrin are used as reaction raw materials which are cheap and easy to obtain; the water is used as a reaction solvent which is environment-friendly and has low cost; no catalyst is used, which has low cost and has no subsequent catalyst recovery trouble; the alpha-amino cyclo nitrile compound is prepared by a one-pot method, and the preparation route is short and the operation is simple; a reaction liquid only needs to undergo simple steps such as organic solvent extroperation, washing, dewatering and drying, organic solvent recovery and the like to obtain the high qualified product, and complicated processing steps such as column chromatography purification is not necessary; the prepared product has high purity of more than 91% and high yield of more than 90%; and the method can be operated continuously, has great production capacity, short production cycle and short production cost, and can be applied to industrialized mass production.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a preparation method of a class of organic compounds. Background technique [0002] α-Aminocyclonitrile compounds are an important class of pharmaceutical intermediates, which can be used to synthesize a variety of drugs for treating psychosis. The Strecker reaction is a classic method for the synthesis of α-aminonitrile compounds, which involves the reaction of aldehydes (or ketones), amines (or ammonia) and cyanide (or hydrocyanic acid) to generate α-aminonitriles. The Strecker reaction mechanism is mainly divided into two parts. The first part is the nucleophilic addition of aldehyde (or ketone) and amine (or ammonia) to remove a molecule of water to generate imine, and the second part is the reaction of cyanide (or hydrocyanic acid) to imine. nucleophilic addition. Early cyanide mainly used hydrocyanic acid, sodium cyanide, potassium cyanide, etc., but because hydrocyanic acid...

Claims

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Application Information

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IPC IPC(8): C07B43/08C07C253/00C07C255/46C07D295/145
Inventor 吴传隆朱伟罗财能王晓萍何咏梅张琳
Owner CHONGQING UNISPLENDOUR CHEM
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