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Synthesis method of cyclobutylamine

A synthesis method and technology of cyclobutylamine, applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as potential safety hazards, and achieve the effects of mild synthesis conditions, convenient industrial production, and easy-to-obtain raw materials

Inactive Publication Date: 2019-11-22
上海迈法生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problem of potential safety hazard caused by the use of azide compounds or metal hydrides in the existing synthetic method of cyclobutylamine, the object of the invention is to provide a synthetic method of cyclobutylamine, using cyclobutanone as raw material, and Ammonia, hydrogen or react with organic amines and hydrogen to generate cyclobutylamine, the synthesis method is safe, environmentally friendly and suitable for industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In a 100 ml autoclave, add 10 g of cyclobutanone, 50 ml of toluene, 0.1 g of palladium carbon (the mass fraction of palladium in the palladium carbon is 10%) and 5 g of ammonia in turn while stirring. Feed hydrogen, keep the hydrogen pressure of feeding at 20-30atm, control the reaction temperature at 30-40°C, react for 24 hours, gas chromatograph monitors that cyclobutanone disappears, end the reaction, filter to remove palladium carbon, rectify the filtrate, collect The fraction with a boiling point of 85-86°C was used to obtain 6.5 g of cyclobutylamine, with a yield of 65% and a purity of 98.5%.

Embodiment 2

[0034] In a 100 ml autoclave, add 10 g of cyclobutanone, 50 ml of ethylene glycol monomethyl ether, 2 g of Raney nickel and 5 g of ammonia successively while stirring, and feed hydrogen into the autoclave to keep feeding The hydrogen pressure is 30-35atm, the reaction temperature is controlled at 30-40°C, the reaction is 24 hours, the gas chromatograph monitors the disappearance of cyclobutanone, the reaction is ended, the Raney nickel is removed by filtration, the filtrate is rectified, and the boiling point is collected at 85-86°C The fraction obtained 4.2 grams of cyclobutylamine, the yield was 42%, and the purity was 98.0%.

Embodiment 3

[0036] In a 100 ml autoclave, add 10 g of cyclobutanone, 20 g of benzylamine, 20 g of toluene, and 0.2 g of palladium carbon in turn while stirring, heat to 40°C and keep for 10 hours; The pressure of the hydrogen gas introduced was 30atm, and the temperature was continued to rise to 80°C, and the reaction was carried out for 24 hours. The cyclobutanone was monitored by a gas chromatograph and the reaction was terminated. The palladium carbon was removed by filtration, the filtrate was rectified, and the fractions with a boiling point of 85-86°C were collected to obtain 7.2 grams of cyclobutylamine, yield 72%, purity 98.0%.

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Abstract

The invention discloses a synthesis method of cyclobutylamine. The synthesis method comprises the following steps: S1, respectively adding cyclobutanone, an organic solvent, a catalyst and ammonia gasinto an autoclave while stirring; and S2, introducing hydrogen into the autoclave, and reacting the mixture for 12-36 h, with the pressure of the introduced hydrogen being maintained at 20-30 atm, and the reaction temperature being controlled to be 0-100 DEG C. According to the synthesis method, raw materials are easy to obtain, synthesis conditions are mild, special safety measures are not needed, and industrial production is facilitated.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of cyclobutylamine. Background technique [0002] Cyclobutylamine is a commonly used intermediate in the synthesis of small molecule drugs. Organic Synthesis Vol47, p28-31, 1967 reported the use of azides to synthesize cyclobutylamine, which are dangerous and toxic. Science of synthesis 2010, Vol41, p1-258 reported that metal hydrides were used to participate in the reaction to synthesize cyclobutylamine. Metal hydrides have potential safety hazards, special safety measures are required, and they are harmful to the environment. [0003] At present, there is an urgent need to seek a safe and environmentally friendly method to prepare cyclobutylamine. Contents of the invention [0004] In order to solve the problem of potential safety hazard caused by the use of azide compounds or metal hydrides in the existing synthetic meth...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C211/35
CPCC07C209/26C07C2601/04
Inventor 黄国强
Owner 上海迈法生物科技有限公司
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