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Preparation method of pridinol mesylate

A technology of predinol and methanesulfonic acid, applied in the field of preparation of predinol mesylate, can solve problems such as long route and low yield, and achieve the effects of simple post-processing, short synthesis route and reduced raw material cost

Inactive Publication Date: 2015-01-07
HUBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The route of this process is long, and the yield in the report is also low

Method used

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  • Preparation method of pridinol mesylate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Methyl acrylate (688.72g, 8mol) was added to a 1L three-necked flask, and piperidine (681.2g, 8mol) was added to a constant pressure dropping funnel, and quickly added dropwise to the three-necked flask within 30min, and the dropwise addition was completed. Heated to 110°C, the reaction system was refluxed, and the reaction was tracked by GC. The reaction is about 2-3h, and the methyl acrylate in the reaction system disappears. Distilled under reduced pressure, and collected fractions at 72-75°C / 2mmHg to obtain methyl 3-(1-piperidinyl)propionate (1367.3 g, yield 99.81%) as a colorless transparent liquid, which was ready for use.

Embodiment 2

[0019] Magnesium (36.5 g, 1.50 mol) and a small amount of iodine were added to a three-necked flask equipped with a mechanically stirred reflux condenser and a drying tube. Bromobenzene (204.12g, 1.30mol) was added with 1L tetrahydrofuran to prepare a solution of bromobenzene in tetrahydrofuran, and the solution of bromobenzene in tetrahydrofuran was added dropwise to the reaction system to keep reflux in the system. magnesium bromide Grignard reagent.

[0020] Add 3-(1-piperidinyl)methyl propionate (85.70 g, 0.50 mol) prepared in Example 1 into a three-necked flask equipped with mechanical stirring and a drying tube, add 300 mL of tetrahydrofuran, cool to 0 ° C, and start to drop After the addition of phenylmagnesium bromide Grignard reagent was completed, the temperature was raised to 66°C, and the reaction was stirred under reflux for 3h. Then the reaction system was cooled to 0° C., and 1 L of 4M HCl solution was added dropwise for hydrolysis. After the hydrolysis is com...

Embodiment 3

[0022] Add pridinol (110.21 g, 0.37 mol) and 600 ml of diethyl ether into a 1 L three-necked flask, and cool to -15°C. Add 200ml of ether to methanesulfonic acid (53.35g, 0.56mol) to make methanesulfonic acid ether solution, add dropwise the methanesulfonic acid ether solution into the three-necked flask, during the dropping process, a white solid will precipitate out, keep stirring for 30min after dropping . After the reaction was completed, it was filtered, the filter cake was washed with 2×200ml ether, and dried in vacuum at 70° C. to obtain a white solid of pritinol mesylate (124.7 g, yield 86.08%).

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Abstract

The invention discloses a preparation method of pridinol mesylate. The preparation method comprises the following steps: carrying out reaction on methyl acrylate and piperidine to obtain methyl 3-(1-piperidyl) propionate, carrying out reaction on methyl 3-(1-piperidyl) propionate and phenyl magnesium bromide (as a Grignard reagent) to obtain pridinol, and forming a salt by pridinol and methanesulfonic acid in a solvent such as an ether solvent to obtain pridinol mesylate as a final product. The process route is simple in synthetic steps, is short in reaction route, is high in yield and is economical and practical.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method of pridinol mesylate. Background technique [0002] Pridinol Mesylate (Pridinol Mesylate), its chemical name is 1,1-diphenyl-3-piperidinyl-1-propanol mesylate, the same as Pridinol Hydrochloride, is a kind of Centrally acting anticholinergics with skeletal muscle relaxants. The preparation of pridinol mesylate is more widely used in the treatment of muscle spasms and movement disorders accompanied by pain or contraction (such as low back pain, neck, shoulder and wrist syndrome, shoulder arthritis, spinal deformation, etc.) and Parkinson's disease. disease. [0003] In the synthesis process of pritinol mesylate reported in Chinese patent CN201210035389, chloroethanol is used as raw material to react with piperidine to obtain 2-piperidinyl ethanol, and 2-piperidinyl ethanol is reacted with magnesium after halogenation to obtain Grignard reagent , Grignard r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/092C07C303/32C07C309/04
CPCC07D295/092
Inventor 王薇周宝晗孙丹胡立新李陵岚缪军锋任家强
Owner HUBEI UNIV OF TECH
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