Preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride
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A technology of hexamethylenetetraammonium chloride and hexamethylenetetramine, which is applied in the field of medicine, can solve the problems of product yield decline, low residue limit, and inapplicability to industrial production, and achieve simplified post-processing steps and solvents. Low cost and simple post-processing effects
Active Publication Date: 2017-10-24
SHANDONG CHENGCHUANG PHARMA R&D
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And as the feeding amount of 3,4-dichlorobenzyl chloride increases, the yield of the product will decrease, and it will be unstable, and a relatively obvious amplification effect will appear
[0009] Method 2 is similar to method 1, using chloroform as a solvent, the applicant has carried out process investigation according to this method, and found that N-(3,4-dichlorobenzyl) hexamethylene tetraammonium chloride was prepared by this method, The purity of the product is about 98%, and the yield is about 85%. Although some conditions have been optimized, it is difficult to improve the purity and yield
In addition, the price of chloroform is higher than that of ethanol, and it belongs to the third category of precursor chemicals. The purchase procedures are cumbersome, and chloroform belongs to the second category of organic solvents in pharmaceutical organic solvents. Industrial production of pharmaceuticals
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Embodiment 1
[0026] Embodiment 1 (single ester solvent):
[0027] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of ethyl acetate, and add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq) under stirring at room temperature , then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with ethyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 154.6g of N-(3,4-dichlorobenzyl)hexamethylene Methyltetraammonium chloride (white powdery solid), yield 94.8%, purity 99.6%, solvent residue 72ppm.
Embodiment 2
[0028] Embodiment 2 (single ester solvent):
[0029] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of isopropyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with isopropyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 151.4g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 92.8%, purity 99.3%, solvent residue 94ppm.
Embodiment 3
[0030] Embodiment 3 (single ester solvent):
[0031] Add 74.9g of hexamethylenetetramine (urotropine) (534.6mmol, 1.1eq) into 475mL of n-butyl acetate, stir at room temperature, add 95g of 3,4-dichlorobenzyl chloride (486mmol, 1.0eq ), then heated to 75°C, reacted for 6 hours, stopped heating, stirred and cooled to crystallize, filtered, washed with n-butyl acetate, and dried in vacuum at 50°C for 4 hours to obtain 149.3g N-(3,4-dichlorobenzyl) Hexamethylenetetraammonium chloride (white powdery solid), yield 91.5%, purity 99.1%, solvent residue 102ppm.
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Abstract
The invention discloses a preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetra-ammoniumchloride. The method comprises the following steps: adding hexamethylene tetra-amine into an organic solvent, stirring at room temperature, adding 3,4-dichlorobenzyl chloride in the stirring process, heating until the reaction is finished, stirring to cool and crystallize, filtering, washing and drying to obtain the N-(3,4-dichlorobenzyl)hexamethylene tetra-ammoniumchloride, wherein the organic solvent is any one or two of ethyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, tert-butyl acetate, n-amyl acetate, isoamyl acetate or propyl propionate. The yield is stable and can reach above 90 percent, the step of removing the solvent is not related, further purification is not needed, aftertreatment is simple, and a product with the purity being above 99 percent can be obtained through direct washing and filtering. Amplification effect is avoided, the solvent cost is low, and the preparation method of the N-(3,4-dichlorobenzyl)hexamethylene tetra-ammonium chloride is particularly suitable for industrialized production.
Description
technical field [0001] The invention relates to a preparation method, in particular to a preparation method of N-(3,4-dichlorobenzyl)hexamethylene tetraammonium chloride. It belongs to the field of medical technology. Background technique [0002] N-(3,4-dichlorobenzyl)hexamethylenetetraammonium chloride is a raw material for the synthesis of 3,4-dichlorobenzylamine, and 3,4-dichlorobenzylamine is the synthesis of 1- A key intermediate of (3,4-dichlorobenzyl)-5-octylbiguanide (Olanexidine). Alkylguanidines have biological activity and are often used as agricultural fungicides and disinfectants. Alkylguanidine disinfectants are easily soluble in water and easy to use because they are made into salts. At the same time, due to their broad-spectrum antibacterial and low toxicity, their bactericidal scope is becoming wider and wider. They are not only used for surface disinfection in hospitals, In addition to disinfection in the food and alcoholic beverage industry, it is also...
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