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Preparation method of phenylephrine hydrochloride impurity

A technology for phenylephrine hydrochloride and epinephrine, applied in the field of 2--1-(3-hydroxyphenyl)ethanol, phenylephrine hydrochloride impurity D

Active Publication Date: 2014-02-05
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Impurity D and its synthesis method, no report

Method used

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  • Preparation method of phenylephrine hydrochloride impurity
  • Preparation method of phenylephrine hydrochloride impurity
  • Preparation method of phenylephrine hydrochloride impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation method 1 of impurity D

[0026] Add 300 mL of water and 30 g of benzyl phenylephrine hydrochloride to a 1L reaction flask, stir until dissolved, slowly add 10 g of sodium borohydride under stirring, gas is generated, after adding sodium borohydride, at room temperature (20-30 ℃) under stirring, liquid phase detection, impurity D peak area percentage 92%. After the reaction is completed, add ammonia water to adjust the pH value to 9-10, then add 200 mL of dichloromethane, stir for 15 minutes, let stand for 15 minutes, and perform layering, the upper layer is an aqueous phase, the lower layer is an organic phase, the organic phase is reserved, and the aqueous phase is Extract with dichloromethane twice, each time with 100 mL of dichloromethane, combine the organic phases, and concentrate under reduced pressure until there are no droplets to obtain the crude product of impurity D, which is a brown oil with a purity of 96%. Recrystallization w...

Embodiment 2

[0027] Embodiment 2: the preparation method 2 of impurity D

[0028] Add 3 mL of tetrahydrofuran and 0.5 g of benzyl phenylephrine to a 10-mL reaction flask, stir, and a white suspension is obtained. Slowly add 0.5 g of lithium aluminum hydride under stirring. After adding, stir at room temperature (20-30 °C). , liquid phase detection, impurity D peak area percentage 82%. After completion of the reaction, filter, concentrate the filtrate to dryness, add 10 mL of dichloromethane and 10 mL of water, carry out layering, retain the organic phase, and concentrate under reduced pressure until there are no droplets to obtain a crude product of impurity D, a brown oil with a purity of 84 %. Recrystallization from 2ml ethyl acetate gave impurity D, about 0.26g, yield 52%, purity 93.5%

Embodiment 3

[0029] Embodiment 3: Different recrystallization solvents are on the preparation yield of impurity D, the influence of quality:

[0030] According to the preparation method 1 of impurity D, the selected recrystallization reagents are respectively: the mixed solvent of ethanol, ethyl acetate, butyl acetate, ethanol and butyl acetate, complete 4 experiments, obtain 4 samples, the yield, the quality data See the table below:

[0031]

[0032]

[0033] Conclusion: The recrystallization reagent adopts the mixed reagent of ethanol and butyl acetate, and the yield and quality are relatively best.

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Abstract

The invention belongs to the field of pharmaceutical chemistry and discloses a phenylephrine hydrochloride impurity D, namely 2-(N-benzyl methylamino)-1-(3-hydroxyl phenyl) alcohol and a preparation method thereof. An impurity D is one of main impurities of crude drugs of phenylephrine hydrochloride; the phenylephrine hydrochloride impurity D is synthesized, a reference substance is provided for examination and quantitative and qualitative analysis of the phenylephrine hydrochloride impurity, so that the quality standards of phenylephrine hydrochloride are improved, and guidance is provided for safe medication of phenylephrine hydrochloride; meanwhile, an effective test basis is provided for obtaining phenylephrine hydrochloride which satisfies EP (European Pharmacopeia) quality standards; the figure 1 is an impurity D H-nuclear magnetic resonance spectrogram.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and discloses a phenylephrine hydrochloride impurity D, namely 2-(N-benzylmethylamino)-1-(3-hydroxyphenyl)ethanol, and a preparation method thereof. Background technique [0002] Phenylephrine hydrochloride is an alpha adrenergic receptor agonist, a sympathomimetic amine that acts directly on the receptor, but sometimes indirectly by promoting the release of phenylephrine from the storage site. Acts on α receptors (especially skin, mucous membranes, internal organs, etc.), causing vasoconstriction, increased peripheral resistance, and increased systolic and diastolic blood pressure. Has obvious vasoconstriction effect. Its effect is similar to that of phenylephrine, but it is weaker and longer-lasting and less toxic. It can reflexively excite the vagus nerve, slow down the heart rate, and have a brief pupil dilation effect. Clinically, it is generally used for infectious toxicity, anaphylact...

Claims

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Application Information

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IPC IPC(8): C07C215/60C07C213/00
Inventor 郭亚兵朱墨杨波耿海明
Owner WUHAN WUYAO SCI & TECH
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