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Synthesis method of intermediate cycloheptanone of guanethidine sulfate drug

A technology of guanethidine sulfate and its synthesis method, which is applied in the field of synthesis of cycloheptanone, a drug intermediate of guanethidine sulfate, can solve problems such as slow onset of action, reduce intermediate links, increase reaction yield, and reduce reaction rate. Effect of temperature and reaction time

Inactive Publication Date: 2017-02-22
厦门莱恩斯特信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Guanethidine sulfate is used as an antihypertensive drug. After oral administration, the onset of effect is slow, and the antihypertensive effect reaches its peak in 3 to 4 days. The effect is strong and long-lasting

Method used

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  • Synthesis method of intermediate cycloheptanone of guanethidine sulfate drug

Examples

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Effect test

example 1

[0012] (i) In a reaction vessel equipped with a stirrer, a thermometer, and a dropping funnel, add 500ml of water, 1.5mol of aluminum powder, and a phosphoric acid solution with a mass fraction of 40%, so that the temperature of the solution is controlled at 60°C, and dropwise add nitromethyl Cycloethanol 1.2mol, after adding, keep the solution temperature at 40°C, add 30mL sulfuric acid solution with a mass fraction of 40% every 30min, add 3 times in total, keep the pH of the solution at 3 for 1h, then filter, the filtrate is aminomethyl Cycloethanoic aluminum sulfate solution, the filtrate cake is used for the next batch after being washed with solvent methanol;

[0013] (ii) Use sulfuric acid to adjust the pH of the solution to 2 °C, slowly add 1.5 mol of sodium sulfite dissolved in 200 ml of water to form a solution, control the reaction temperature at 3 °C, keep the constant temperature for 20 minutes after adding, and then raise the temperature to 30 ℃, the reaction time...

example 2

[0015] (i) In a reaction vessel equipped with a stirrer, a thermometer, and a dropping funnel, add 550 ml of water, 1.5 mol of metal zinc powder, and a phosphoric acid solution with a mass fraction of 45%, so that the temperature of the solution is controlled at 65° C. Cycloethanol 1.2mol, after the addition, keep the solution temperature at 45°C, add 30mL of sulfuric acid solution with a mass fraction of 43% every 30min, add 3 times in total, keep the pH of the solution at 3 for 1h, then filter, the filtrate is ammonia Cycloethanoic zinc sulfate solution, the filtrate cake is used for the next batch after being washed with methyl ether solvent;

[0016] (ii) Use sulfuric acid to adjust the pH of the solution to 3, reduce the temperature of the solution to 4°C, slowly add 1.7mol of sodium sulfite dissolved in 200ml of water to form a solution, control the reaction temperature at 4°C, keep the constant temperature state for 20 minutes after adding, and then raise the temperature...

example 3

[0018] (i) In a reaction vessel equipped with a stirrer, a thermometer, and a dropping funnel, add 600ml of water, 1.5mol of metal aluminum powder, and a phosphoric acid solution with a mass fraction of 50%, so that the temperature of the solution is controlled at 70°C, and dropwise add nitrate Cycloethanol 1.2mol, after the addition, keep the solution temperature at 50°C, add 30mL sulfuric acid solution with a mass fraction of 45% every 30min, add 3 times in total, keep the pH of the solution at 4 for 1h, then filter, the filtrate is ammonia Cycloethanoic aluminum sulfate solution, the filtrate cake is used for the next batch after washing with methanol solvent;

[0019] (ii) Use sulfuric acid to adjust the pH of the solution to 3, reduce the temperature of the solution to 5°C, slowly add 2mol of sodium sulfite dissolved in 200ml of water to form a solution, control the reaction temperature at 5°C, keep the constant temperature state for 20 minutes after adding, and then raise...

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Abstract

A synthesis method of intermediate cycloheptanone of a guanethidine sulfate drug comprises the steps as follows: (i) 500-600 ml of water, 1.5 mol of metal powder and a phosphoric acid solution with the mass percentage being 40% -50% are added to a reaction vessel equipped with a stirrer, a thermometer and a dropping funnel, the temperature of the solution is controlled to be 60-70 DEG C, 1.2 mol of nitromethylcyclohexanol is added dropwise, the temperature of the solution is maintained to be 40-50 DEG C after addition, 30 mL of a sulfuric acid solution with the mass percentage being 40%-45% is added at an interval of 30 min and is added 3 times altogether, the pH of the solution is maintained to be 3-4 for 1 h, the filtrate is an aminomethyl cyclohexanol sulfate solution, and the filter cake is washed with a solvent and used for the next batch; (ii) pH of the solution is adjusted with sulfuric acid to be 2-3, the solution temperature is reduced to 2-5 DEG C, 1.5-2 mol of a sodium sulfite solution is added slowly and dissolved in 200 ml of water, the temperature is increased to 30-35 DEG C, distillation is performed through steam until no oily substances are distilled off, an oil layer is separated, a water layer is extracted with a solvent for 10-15 times, the oil layer and the solvent layer are combined, a solvent is distilled off under atmospheric pressure, distilling under reduced pressure is performed, a fraction at 65-70 DEG C is collected, and cycloheptanone is obtained.

Description

technical field [0001] The invention relates to a method for synthesizing cycloheptanone, a pharmaceutical intermediate of guanethidine sulfate. Background technique [0002] Guanethidine sulfate is used as an antihypertensive drug. After oral administration, the onset of effect is slow, and the antihypertensive effect reaches its peak in 3 to 4 days. The effect is strong and long-lasting. When the blood pressure is lowered, the heart rate is slowed down, the cardiac output is reduced, and the pulse pressure is reduced. Intravenous injection of large doses begins to excrete more norepinephrine and prevents reabsorption of vesicles, causing blood pressure to rise. Chronic administration begins to lower blood pressure due to the inability to release transmitters. Long-term medication replaces the transmitter stored in the vesicle and releases the transmitter, and then prevents the uptake and synthesis of the transmitter, so that the transmitter is exhausted and blood pressur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C49/413C07C49/403
CPCC07C45/00C07C213/02
Inventor 彭响亮
Owner 厦门莱恩斯特信息科技有限公司
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