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Preparation of mizolastine intermediate

A methylaminopiperidine and reaction technology, applied in the field of industrial synthesis of 4-methylaminopiperidine, can solve the problems of complex process, low yield, and many waste water, and achieve the effects of simplified process, high yield and environmental friendliness

Inactive Publication Date: 2011-08-03
LIAONING BENYUAN PHARMACY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The process is complicated, the yield is low, and the waste water is more

Method used

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  • Preparation of mizolastine intermediate
  • Preparation of mizolastine intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1 prepares 4-methylaminopiperidine

[0016] Methylammonia-methanol solution: 65Kg of anhydrous methanol is added to the kettle, the temperature is lowered to below 20°C, and 3Kg of methylammonia is passed through to obtain a 0.05% methylammonia-methanol solution. Add 70Kg of methylamine-methanol solution to a 100L enamel reaction kettle, add 10Kg of piperidone hydrochloride, and stir at 20-25°C for 10-12 hours. Transfer to a high-pressure reactor, add 5.42L of 30% ammonia water, 0.8Kg of Raney nickel, a pressure of 1Mpa, a temperature of 25-30°C, and a stirring speed of 400 rpm. The reaction was stirred for 2 hours, and the plate was sampled to determine the end point of the reaction. The pressure is released and the material is discharged. The methanol is first evaporated under normal pressure and then under reduced pressure to obtain 5.0-5.1Kg (5-6.5Kg) of the product.

Embodiment 2

[0017] Example 2 Preparation of 1-{1-(4-fluorophenyl)methyl-1H-benzimidazol-2-yl}-N-methyl-4-piperidinamine

[0018] Put methamphetamine, flubenzimidazole and water into the reaction kettle, control the temperature at 120°C, stir and react for 10 hours, and monitor the reaction by spotting the plate. After the reaction is complete, cool down, filter, evaporate to dryness to remove water, add 12Kg 36% hydrochloric acid, stir for one hour and filter, the filtrate is extracted with 80Kg chloroform, spot plate, after passing the test, the water layer is adjusted to PH=13 with 20% sodium hydroxide, and a solid is precipitated. Filter, wash the filter cake with water, and dry it in the air. Filter and dry to obtain the product (5-6Kg).

Embodiment 3

[0019] Embodiment 3 prepares mizolastine

[0020] Put piperidinamine and methylthiopyrimidinone into a 3L three-necked reaction flask, reduce the pressure to 1-10mmHg with a vacuum pump, heat in an oil bath to 100°C, stir mechanically for ten hours, cool, knock out, and pulverize to obtain 1.1-1.2Kg.

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Abstract

The invention discloses a method for industrially synthesizing a compound which is as shown in a formula (I). The method is characterized by reacting 4-piperidone with methylamine so as to generate 4-piperidone ketimine, and carrying out hydrogenzation reduction so as to obtain 4-methylamino piperidine as shown in the formula I. The product synthesized by the method has the advantages of high purity, simple post process and high yield, and the compound as shown in the formula (I) is used for synthesis of mizolastine.

Description

technical field [0001] The invention relates to a new method for industrial synthesis of 4-methylaminopiperidine, which is used for the synthesis of mizolastine. Background technique [0002] Mizolastine is a second-generation antihistamine drug, which not only has a strong antihistamine effect, but also has the effect of inhibiting other inflammatory transmitters. Such as inhibiting the production of leukotrienes, reducing edema and so on. Mizolastine has both antihistamine, antiallergic and anti-inflammatory effects, and is the preferred drug for the treatment of acute urticaria. Clinical studies have shown that its efficacy in treating acute urticaria is significantly better than other antihistamines. The invention relates to a new method for industrially synthesizing 4-methylaminopiperidine and the application of the compound in the industrial production of mizolastine. More specifically, the present invention relates to a process for the industrial synthesis of a com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58C07D211/02C07D401/14
Inventor 颜文革漆新国李昕昊李学坤刘念
Owner LIAONING BENYUAN PHARMACY CO LTD
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