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A kind of preparation method of phenylephrine hydrochloride impurity

A technology of phenylephrine hydrochloride and epinephrine, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of aminohydroxyl compounds, etc.

Active Publication Date: 2015-11-18
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Impurity D and its synthesis method, no report

Method used

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  • A kind of preparation method of phenylephrine hydrochloride impurity
  • A kind of preparation method of phenylephrine hydrochloride impurity
  • A kind of 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 300mL of water and 30g of benzylphenylephrine hydrochloride into a 1L reaction bottle, stir until dissolved, slowly add 10g of sodium borohydride under stirring, and gas will be generated. ℃), and liquid phase detection, the peak area percentage of impurity D was 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 the water phase, and the lower layer is the organic phase. Then extract with dichloromethane twice, each time with 100 mL of dichloromethane, combine the organic phases, concentrate under reduced pressure until there is no liquid drop, and obtain the crude impurity D, which is a brown oily product with a purity of 96%. Recrystallize from 15m ethanol and 30ml butyl acetate to obtain impurity D, about 16.6g, yield 62.9%, purity 99.5%

Embodiment 2

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

[0028] Add 3mL of tetrahydrofuran and 0.5g of benzylphenylephrine into a 10ml reaction bottle, stir to form a white suspension, slowly add 0.5g of lithium aluminum hydride under stirring, after the addition, stir at room temperature (20-30°C) , liquid phase detection, impurity D peak area percentage 82%. After the reaction was completed, filter and concentrate the filtrate to dryness, then add 10 mL of dichloromethane and 10 mL of water for layering, keep the organic phase, concentrate under reduced pressure until there is no liquid drop, and obtain the crude product of impurity D, a brown oily substance with a purity of 84 %. Recrystallize from 2ml ethyl acetate to obtain impurity D, about 0.26g, yield 52%, purity 93.5%

Embodiment 3

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

[0030] According to the preparation method 1 of impurity D, the recrystallization reagents were selected to be: ethanol, ethyl acetate, butyl acetate, a mixed solvent of ethanol and butyl acetate, and 4 experiments were completed to obtain 4 samples. The yield and 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 α-adrenergic receptor agonist, a sympathomimetic amine that acts directly on the receptor, but sometimes also works indirectly by promoting the release of phenylephrine from the storage site. Acting on α-receptors (especially skin, mucous membranes, internal organs, etc.), causing vasoconstriction, increasing peripheral resistance, and increasing systolic and diastolic blood pressure. It has obvious vasoconstriction effect. Its effects are similar to those of phenylephrine, but are weaker, longer lasting, and less toxic. It can reflexively excite the vagus nerve, slow down the heart rate, and temporarily dilate the pupils. It is generally used clinically for infection, poisoning, ana...

Claims

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Application Information

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