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A kind of preparation method of doxylamine succinate

A technology for doxylamine and pyridyl phenylmethyl methanol, which is applied in the fields of medical technology and organic synthesis, can solve the problems of complicated post-processing, difficulty in ensuring product yield and purity, low reaction efficiency and the like, and achieves simple post-processing. , the effect of high product yield and purity, and high reaction efficiency

Active Publication Date: 2016-05-04
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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  • A kind of preparation method of doxylamine succinate
  • A kind of preparation method of doxylamine succinate
  • A kind of preparation method of doxylamine succinate

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preparation example Construction

[0032] The preparation of embodiment 12-pyridyl phenyl methyl carbinol

[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...

Embodiment 42

[0039] The preparation of embodiment 42-pyridylphenylmethylmethanol

[0040] Add 9.6g (0.40mol) of magnesium chips activated by dilute hydrochloric acid into a 1000ml three-neck flask, add 100ml of ether and 1 grain of iodine; then slowly drop 80.4g (0.4mo) of iodobenzene mixed with 50ml of ether into 10ml, wait until the red The brown color turns light yellow and starts to reflux, the remaining iodobenzene is added dropwise, the solution changes from light yellow to milky white, and gradually turns gray again, after dropping, stir and reflux for 15 hours, add 12.1g (0.1mol) of 2-acetylpyridine Mix 50ml of diethyl ether 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 dripping, separate and retain the organic phase, extract the water phase with 2×300ml ether once...

Embodiment 5

[0043] The synthesis of embodiment 5 doxylamine

[0044]

[0045] Add 16g (0.4mol) of sodium amide and 100mL of xylene into a 1000mL three-necked flask and heat to 140°C; mix 50g (0.25mol) of 2-pyridylphenylmethylmethanol with 250mL of xylene dropwise into the above reaction system, and reflux reaction under these conditions for 5h; 108g (1.0mol) of dimethylaminochloroethane mixed with 200mLl xylene solution was slowly dropped into the reaction system, and refluxed for 3-4h. After the reaction was completed, 100 mL of saturated NH 4 Cl aqueous solution, stir for 0.5h, add 400mL of water, adjust the pH value to 2~3, discard the organic phase, keep the water phase, extract the water phase with 100mL×2 ethyl acetate, discard the organic phase; adjust the pH value of the water phase to 5~6, add, extract with 2×200mL ethyl acetate, discard the organic phase, this step can remove most of the unreacted 2-pyridylphenylmethylcarbinol and some impurities; adjust the pH value of 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 (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, has 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, producing 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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