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Cyclohexyl biguanide hydrochloride and preparation method thereof

A technology of cyclohexaformin hydrochloride and n-hexanol, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve problems such as toxicity and poor solubility of dicyandiamide

Active Publication Date: 2021-05-18
XI'AN PETROLEUM UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, xylene has certain toxicity; in addition, xylene has the disadvantage of poor solubility to dicyandiamide

Method used

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  • Cyclohexyl biguanide hydrochloride and preparation method thereof
  • Cyclohexyl biguanide hydrochloride and preparation method thereof
  • Cyclohexyl biguanide hydrochloride and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] This embodiment includes the following steps:

[0025] In a 100mL three-necked flask, install a mechanical stirrer, a reflux condenser, and a thermometer. First add 6.9g of ammonium chloride and 50mL of n-pentanol, then add 11.5mL of cyclohexylamine at one time while stirring, pour in condensed water, heat to 70-80°C and keep it for 30 minutes, then quickly raise the temperature to 135-145°C for 4.5 hours . After that, the temperature was lowered to 80°C, 10 g of dicyandiamide was added, and the temperature was raised to 136-145°C to react for 5.5 hours. After cooling to 90°C, add 55mL of distilled water to the reaction mixture, raise the temperature to 90-95°C and keep stirring for 50 minutes, the product enters the water phase; collect the water phase, spin the water phase to concentrate and precipitate the crude product. Use 65 mL of 85% ethanol-water as the recrystallization solvent for the crude product, add 1 g of activated carbon after heating to dissolve, refl...

Embodiment 2

[0027] This embodiment includes the following steps:

[0028] In a 100mL three-necked flask, install a mechanical stirrer, a reflux condenser, and a thermometer. First add 6.5g of ammonium chloride and 40mL of isoamyl alcohol, then add 10.4ml of cyclohexylamine at one time while stirring, pour in condensed water, heat to 70-80°C and keep it for 60 minutes, then quickly raise the temperature to 135-145°C for 3.5 hours . After that, the temperature was lowered to 75°C, 9.2 g of dicyandiamide was added, and then the temperature was raised to 136-145°C to react for 4.5 hours. Then lower the temperature to 85°C, add 50mL of distilled water to the reaction mixture, raise the temperature to 95-100°C and keep stirring for 40 minutes, the product enters the water phase; collect the water phase, rotate the water phase to concentrate and precipitate the crude product. Use 55 mL of 80% ethanol-water as the recrystallization solvent for the crude product, add 0.8 g of activated carbon af...

Embodiment 3

[0030] This embodiment includes the following steps:

[0031] In a 100mL three-necked flask, install a mechanical stirrer, a reflux condenser, and a thermometer. First add 6.45g of ammonium chloride and 36mL of n-hexanol, then add 11.0mL of cyclohexylamine at one time while stirring, pour in condensed water, heat to 70-80°C and keep it for 50 minutes, then quickly raise the temperature to 135-145°C for 4 hours. Then cool down to 80°C, add 8.4g of dicyandiamide, then raise the temperature to 136-150°C for 2.5 hours. Then lower the temperature to 90°C, add 45mL of distilled water through the upper part of the condenser, raise the temperature to 95-100°C and keep stirring for 45 minutes, the product enters the water phase; collect the water phase, spin the water phase to concentrate and precipitate the crude product. Pour the crude product into a clean 250mL beaker again, use 60mL of 95% ethanol-water as a recrystallization solvent, add 0.7g of activated carbon after heating and...

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Abstract

The invention discloses a cyclohexyl biguanide hydrochloride and a preparation method thereof. The preparation method comprises the following steps: adding 4.5 to 7.5 grams of ammonium chloride, 10 to 12.5 mL of fatty amine and 20 to 90 mL of an organic solvent into a three-neck flask, introducing condensed water, introducing nitrogen at the flow rate of 20 to 50 mL / min, heating to 70 to 80 DEG C under stirring, reacting for 0.5 to 1.5 hours, then heating to 135 to 150 DEG C, and reacting for 2.5 to 5.5 hours; cooling to 60 to 75 DEG C, adding 7.5 to 10.5 grams of dicyandiamide, heating to 135 to 145 DEG C, and continuing to react for 3.5 to 6.5 hours; cooling to 70-85 DEG C, adding 25-55 mL of distilled water, heating to 90-100 DEG C, continuously stirring for 0.5-1.0 hour at the constant temperature, and introducing the product into a water phase; and collecting the water phase, carrying out rotary concentration on the water phase to separate out a crude product, adding 55-80 mL of water containing 80-90% by volume of ethanol into the crude product, heating for dissolving, adding 0.5-1.2 grams of activated carbon, refluxing for 0.5-1.0 hour, filtering while hot to remove insoluble substances, cooling filtrate to 5 DEG C to separate out a product, and drying. The required raw materials are easy to obtain, and the preparation method is simple and convenient and is expected to be used for industrial production.

Description

technical field [0001] The invention relates to the technical field of biguanide hydrochloride preparation, in particular to a cyclohexaformin hydrochloride and a preparation method thereof. Background technique [0002] At present, metformin hydrochloride, which is used for the treatment of type 2 diabetes, has been found to be effective against TPC-1 human papilloma thyroid cancer cells, Eca-109 human esophageal cancer cells, SHSY5Y human neuroblastoma cells, PC-3 human prostate cancer cells, The proliferation of HT-29 human colon cancer cells and HCT-8 human colon cancer cells can be inhibited, revealing that metformin may have a wide range of anti-tumor effects (Yu Jingkun, Han Xuechao, Li Mingzhi, et al. Metformin can inhibit the proliferation of some malignant tumor cells [J]. Journal of East China University of Science and Technology (Medical Science), 2019, 01, 20). Therefore, it is particularly important to research and develop novel biguanide derivatives and syste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/26
CPCC07C277/08C07C2601/14C07C279/26
Inventor 张科良吴亚徐玉乔成钰谢娟
Owner XI'AN PETROLEUM UNIVERSITY
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