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Preparation method of doxylamine succinate

A technology of succinic acid and Westminster, which is applied in the field of medical technology and organic synthesis, can solve the problems of complex post-processing, low reaction efficiency, and difficulty in ensuring product yield and purity, and achieve simple post-processing, high reaction efficiency, and product yield. The effect of high rate and purity

Active Publication Date: 2014-01-22
JIANGSU LEEWAY BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction efficiency of this scheme is low, and the post-treatment is complicated. The melting point of 2-pyridylphenylmethylmethanol is 33-34.5°C, and it is difficult to guarantee the product yield and purity by distillation.

Method used

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  • Preparation method of doxylamine succinate
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  • Preparation method of doxylamine succinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of 2-pyridylphenylmethylcarbinol

[0033]

[0034] Add 13.92g (0.58mol) of magnesium chips activated by dilute hydrochloric acid into a 1000ml three-neck flask, add 300ml of ether and 1 grain of iodine; then slowly drop 114.24g (0.56mo) of iodobenzene into 100ml of ether and drop it into 10ml, wait until the red The brown color turned into light yellow and began to reflux, and the remaining iodobenzene was added dropwise, and the solution changed from light yellow to milky white, and gradually turned gray again. After the drop, stirred and refluxed for 15 hours, 48.20 g (0.4 mol) of 2-acetylpyridine Mix 100ml of diethyl ether and slowly drop into the above solution, the solution turns from gray to yellow, continue to react for 2-3 hours after the drop, after the reaction is completed, add dropwise 100ml of saturated NH 4 Cl aqueous solution, stir while adding, continue to stir for 1h after dripping, separate and retain the organic phase, extract...

Embodiment 2

[0035] Example 2 Preparation of 2-pyridylphenylmethylcarbinol

[0036] Add 13.92g (0.58mol) of magnesium chips activated by dilute hydrochloric acid into a 1000ml three-necked flask, add 300ml of methyl tert-butyl ether and 1 grain of iodine; then mix 114.24g (0.56mo) of iodobenzene with 100ml of methyl tert-butyl ether Slowly add 10ml of butyl ether, wait until the reddish-brown color turns light yellow and starts to reflux, add the remaining iodobenzene dropwise, the solution changes from light yellow to milky white, and gradually turns gray again, stir and reflux for 10 hours after dropping, and then 48.20g (0.4mol) of 2-acetylpyridine mixed with 100ml of methyl tert-butyl ether was slowly dropped into the above solution, the solution turned from gray to yellow, and continued to react for 2 to 3 hours after the completion of the reaction. After the reaction was completed, 100ml of saturated NH 4 Cl aqueous solution, stir while adding, continue to stir for 1h after dripping...

Embodiment 3

[0037] Example 3 Preparation of 2-pyridylphenylmethylmethanol

[0038] Add 7.2g (0.30mol) of magnesium chips activated by dilute hydrochloric acid into a 1000ml three-necked flask, add 100ml of tetrahydrofuran and 1 grain of iodine; then slowly drop 50.0g (0.25mo) of iodobenzene mixed with 50ml of tetrahydrofuran into 10ml, wait until the red The brown color turns light yellow and starts to reflux, the remaining iodobenzene is added dropwise, the solution turns from light yellow to milky white, and gradually turns gray again, after dropping, stir and reflux for 8 hours; Mix 50ml of tetrahydrofuran and slowly drop it into the above solution, the solution turns from gray to yellow, and continue to react for 2-3 hours after the drop; after the reaction is completed, add 100ml of saturated NH 4 Cl aqueous solution, stir while adding, continue to stir for 1h after dropping, separate and retain the organic phase, extract the water phase with 2×200ml tetrahydrofuran once, combine the...

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Abstract

The invention relates to a preparation method of doxylamine succinate. The preparation method comprises the steps as follows: firstly, a Grignard reagent generated by iodobenzene and magnesium reacts with 2-acetylpyridine to generate 2-pyridyl phenyl methyl alcohol, the 2-pyridyl phenyl methyl alcohol is recrystallized to be purified, then the 2-pyridyl phenyl methyl alcohol reacts with sodium amide and 2-dimethylamino chloroethane sequentially, doxylamine is obtained and has a salt forming reaction with succinic acid finally, and the doxylamine succinate is obtained. The preparation method is high in reaction efficiency, lower in cost and applicable to industrial mass production.

Description

technical field [0001] This field belongs to the fields of medical technology and organic synthesis, and in particular relates to a preparation method of an antihistamine drug doxylamine succinate. Background technique [0002] Doxylamine succinate, chemical name N,N-dimethyl-2-[1-phenyl-1-(2-pyridine)ethoxy]ethylamine succinate, CAS number: 562 -10-7, is an ethanol antihistamine drug with antihistamine effect, anticholinergic effect and significant sedative effect, suitable for a variety of allergic skin diseases, hay fever, asthmatic bronchitis, allergic Rhinitis, etc.; it can also be used for short-term treatment of insomnia, which produces drowsiness by inhibiting the central nervous system, which is clinically safe and effective. [0003] Invention patent CN201210587388.0 discloses a preparation method of doxylamine succinate intermediate 2-pyridylphenylmethylmethanol, dissolving acetophenone in methyl tert-butyl ether, and adding boron trifluoride at the same time , ...

Claims

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Application Information

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IPC IPC(8): C07D213/30C07C55/10C07C51/41
CPCC07D213/30
Inventor 包金远宋志春苏梅张孝清蒋玉伟
Owner JIANGSU LEEWAY BIOLOGICAL TECH
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