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Method for preparing 1-cyclohexene ethylamine by selective reduction

A cyclohexeneethylamine, selective technology, applied in the preparation of amino compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high price and high cost of metal hydrides, reduce raw materials and operating costs, The effect of simple operation and easy large-scale production

Inactive Publication Date: 2018-11-16
抚顺东科新能源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The metal hydride (lithium aluminum hydride) used in this method is expensive, and the cost is higher

Method used

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  • Method for preparing 1-cyclohexene ethylamine by selective reduction
  • Method for preparing 1-cyclohexene ethylamine by selective reduction
  • Method for preparing 1-cyclohexene ethylamine by selective reduction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] ①Preparation of crude 1-cyclohexeneethylamine: under the protection of argon, add 121g of 1-cyclohexene acetonitrile (1.0mol 1.0eq) and 800mL of toluene to the reaction flask, and slowly add the red aluminum solution dropwise at 15±5°C 577.6g (2.0mol 2.0eq70%), after about 1 hour, the reaction was stirred at this temperature for 16 hours; it was slowly added dropwise to (10% NaOH) aqueous solution 1500mL to quench the reaction, filtered, and the mother liquor was separated , the aqueous phase was extracted again with 500 mL of toluene, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain 135 g of crude 1-cyclohexeneethylamine.

[0039] ②Preparation of pure 1-cyclohexylethylamine: add 128 g of crude 1-cyclohexylethylamine to the reaction flask, reduce the pressure to 5-10 mmHg, and distill at 70-120 degrees to obtain 1-cyclohexylethylamine Pure vinyl ethylamine 115g, 92%.

Embodiment 2

[0041] ①Preparation of crude 1-cyclohexeneethylamine: under the protection of argon, add 121g of 1-cyclohexene acetonitrile (1.0mol 1.0eq) and 1000mL of tetrahydrofuran to the reaction flask, and slowly add the red aluminum solution dropwise at 15±5 degrees 577.6g (2mol 2.0eq70%), dripped for about 1 hour, then stirred and reacted at this temperature for 20 hours; slowly added it dropwise to (10% NaOH) aqueous solution 1500mL to quench the reaction, filtered, and the mother liquor was separated. The aqueous phase was extracted twice with 500 mL of diethyl ether, the organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent to obtain 132 g of crude 1-cyclohexeneethylamine.

[0042] ②Preparation of pure 1-cyclohexeneethylamine: Add 130g of crude 1-cyclohexeneethylamine to the reaction flask, reduce the pressure to 5-10 mm Hg, and distill at 70-120 degrees to obtain 1-cyclohexene Pure ethylamine 119g, 95%.

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Abstract

The invention discloses a method for preparing 1-cyclohexene ethylamine by selective reduction. The method comprises the following steps: (1) dissolving a raw material 1-cyclohexene acetonitrile in asolvent under the protection of inert gas, then slowly dropwise adding a reducing agent vitride solution at a certain temperature, and reacting at a certain temperature after dropwise adding; quenching by dropwise adding a reaction liquid into an alkali aqueous solution, extracting with an organic solvent, drying with a drying agent, carrying out desolvation with an organic phase to obtain a 1-cyclohexene ethylamine crude product; and (2) heating the 1-cyclohexene ethylamine crude product under a certain vacuum condition for distillation purification so as to obtain a 1-cyclohexene ethylaminepure product. the invention has the following advantages: 1, the vitride solution used in the method has lower toxicity and is cheaper and more easily available, thus greatly reducing raw material andoperational costs; 2, reaction steps of the method are few, the intermediate reaction is easy to control, operation is simple, and the method is easy for large-scale production; and 3, purity and yield of the product prepared by the method are high and both can reach 90% and above.

Description

1. Technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing 1-cyclohexeneethylamine through selective reduction. 2. Background technology [0002] 1-Cyclohexeneethylamine (CAS: 3399-73-3, boiling point: 197.5°C) is an important intermediate in organic synthesis and pharmaceuticals, and is a central antitussive of morphinans—dextromethorphan, Tema Therefore, the preparation of 1-cyclohexeneethylamine is of great significance for the fields of synthetic chemistry and medicine. The main method for synthesizing 1-cyclohexeneethylamine at present is as follows: [0003] Method 1 (indirect synthesis method): 1-cyclohexene acetonitrile is used as raw material, hydrolyzed to 1-cyclohexene acetic acid, acid chlorinated to 1-cyclohexene acetyl chloride, reduced to 1-cyclohexene ethanol, chlorinated Be 1-cyclohexene ethyl chloride, ammonolysis to obtain 1-cyclohexeneethylamine, the specific reaction...

Claims

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Application Information

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IPC IPC(8): C07C209/48C07C211/25
CPCC07C209/48C07C2601/16C07C211/25
Inventor 丛强李婉毛春风胡玉珊刘思含
Owner 抚顺东科新能源科技有限公司