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Preparation method of detomidine hydrochloride

A technology of detomidine hydrochloride and concentrated hydrochloric acid, applied in directions such as organic chemistry, can solve the problems of complicated operation steps, low yield and high cost, and achieve the effects of simple operation steps, high yield and low cost

Inactive Publication Date: 2018-03-20
安徽诺全药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above method has the disadvantages of complex operation steps, low yield or high cost.

Method used

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  • Preparation method of detomidine hydrochloride
  • Preparation method of detomidine hydrochloride
  • Preparation method of detomidine hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment 1 (2,3-dimethylphenyl) (1H-imidazol-4-yl) methanol

[0027] Add 50mL of tetrahydrofuran, 0.72g of magnesium chips, 0.52g of 2,3-dimethylbromobenzene and a grain of iodine into the reaction flask, raise the temperature to reflux to initiate the reaction, then slowly add 5g of 2,3-dimethylbromobenzene, dropwise After the addition, reflux reaction for 1 hour to obtain (2,3-dimethylphenyl)magnesium bromide, then lower the temperature to 50°C, add 0.96g of 1H-imidazole-4-carbaldehyde to it in batches, and then raise the temperature to reflux reaction After 4 hours, cool to 0-10°C, add dropwise 50mL of 2N (mol / L) hydrochloric acid aqueous solution, concentrate under reduced pressure to remove most of tetrahydrofuran, wash the resulting solution with 25mL of methyl tert-butyl ether, and wash the aqueous phase with 20% sodium hydroxide The pH of the aqueous solution was adjusted to 8-9, and a large amount of solid precipitated, filtered, and the fi...

Embodiment 2

[0028] The preparation of embodiment 2 detomidine hydrochloride

[0029] Add 15g of (2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol prepared in Example 1, 100mL of isopropanol and 10mL of concentrated hydrochloric acid into the reaction flask, heat up to reflux for 8 hours, and react The solution was concentrated to 40 mL, cooled to 0-10°C and slowly added 100 mL of isopropyl ether dropwise, the solid was precipitated, kept stirring for 1 hour, filtered, the filter cake was washed with 20 mL of isopropyl ether, and the obtained solid was dried under reduced pressure at 70°C to obtain a white Solid 14.6g, yield 89%. Detect this white solid with nuclear magnetic resonance, the result is as follows: 1 H NMR (400MHz, DMSO-d6) δ9.03(d,1H),7.18(d,1H),7.03-6.94(m,3H),3.99(s,2H),2.17(s,3H),2.10( s, 3H). Its H NMR spectrum is shown in figure 2 As shown, thus it can be determined that this white solid is detomidine hydrochloride.

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Abstract

The invention discloses a preparation method of detomidine hydrochloride. The preparation method comprises the following steps of (1) enabling (2,3-dimethyl phenyl)magnesium bromide and 1H-imidazole-4-formaldehyde to perform addition reaction, so as to obtain an intermediate, namely (2,3-dimethyl phenyl)(1H-imidazole-4-yl)methanol; (2) under the condition of existence of concentrated hydrochloricacid, enabling the (2,3-dimethyl phenyl)(1H-imidazole-4-yl)methanol and isopropanol to perform reduction reaction, so as to obtain the detomidine hydrochloride. The preparation method has the advantages that the operation is simple and convenient, the yield rate is high, and the cost is low.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of detomidine hydrochloride. Background technique [0002] Detomidine hydrochloride (Detomidine), the chemical name is 4-[(2,3-dimethylphenyl)methyl]-1H-imidazole hydrochloride, and the molecular formula is C 12 h 15 C l N 2 , molecular weight is 222.71, has the structure shown in following formula (I): [0003] [0004] Detomidine hydrochloride is a horse sedative that is mediated by activation of α2 catecholamine receptors, resulting in sedative and analgesic effects. At present, the preparation methods of detomidine hydrochloride mainly include methods such as direct condensation, Barluenga boronic acid coupling, and Kisner-Wolf-Huang Minglong reduction. However, the above method has the disadvantages of complex operation steps, low yield or high cost. Contents of the invention [0005] The technical problem to be solved by the pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58
CPCC07D233/58
Inventor 许良志胡志刚何大荣杜小鹏钱祝进何勇刘庄子
Owner 安徽诺全药业有限公司