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A kind of assay method of 3-aminopiperidine enantiomeric excess rate

An enantiomer, aminopiperidine technology, applied in the field of determination of 3-aminopiperidine enantiomeric excess rate, can solve the problem of large sample size requirements, inability, low energy of nitrogen atom lone pair electrons, etc. problem, to achieve the effect of good reproducibility, simple operation and convenient standardized operation

Inactive Publication Date: 2017-06-16
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Although there are two nitrogen atoms in the molecular structure of 3-aminopiperidine, due to the low energy of the lone pair of electrons of the nitrogen atom, 3-aminopiperidine has almost no absorption in the ultraviolet region. -Aminopiperidine becomes weak for accurate and reliable qualitative and quantitative
But in fact, the differential refractive index detector requires a large amount of sample to be analyzed.

Method used

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  • A kind of assay method of 3-aminopiperidine enantiomeric excess rate
  • A kind of assay method of 3-aminopiperidine enantiomeric excess rate
  • A kind of assay method of 3-aminopiperidine enantiomeric excess rate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: ( R Liquid Chromatographic Analysis of )-(+)-1-Phenylethanesulfonyl Chloride and 3-Aminopiperidine Derivatives

[0032] 1-1:( R )-(+)-1-phenylethanesulfonyl chloride and ( RS ) Liquid Chromatographic Analysis of -3-Aminopiperidine Derivatives

[0033] Weigh ( RS )-3-aminopiperidine 3.09g (0.03mol), dissolved in 50mL of dichloromethane, stirred at 5 ° C, slowly added dropwise ( R )-(+)-1-phenylethanesulfonyl chloride 6.14 g (0.03 mol). TLC monitors the reaction, and after the reaction is completed, the solvent is evaporated to obtain ( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives.

[0034] Will( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives are dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography. Liquid chromatography conditions: Dima C18 column, mobile phase is water-acetonitrile (volume ratio 30:70), UV detection wavelength i...

Embodiment 2

[0040] Embodiment 2: 3-aminopiperidine and ( R Study on Derivatization Conditions of )-(+)-1-Phenylethanesulfonyl Chloride

[0041] 2-1:( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-Aminopiperidine Derivatized Liquid Chromatographic Analysis

[0042] Weigh ( RS )-3-aminopiperidine 3.09g (0.03mol), dissolved in 40mL tetrahydrofuran, stirred at 0 ℃, slowly added dropwise ( R )-(+)-1-phenylethanesulfonyl chloride 6.14 g (0.03 mol). TLC monitors the reaction, and after the reaction is completed, the solvent is evaporated to obtain ( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives.

[0043] Will( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives are dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography. Liquid chromatography conditions: Dima C18 column, mobile phase is water-acetonitrile (volume ratio 30:70), UV detection wavelength is 254nm, flow rate...

Embodiment 3

[0062] Embodiment 3: chromatographic condition investigation test

[0063] (1) Derivatization

[0064] Weigh ( RS )-3-aminopiperidine 3.09g (0.03mol), dissolved in 50mL of dichloromethane, stirred at 5°C, slowly added dropwise ( R )-(+)-1-phenylethanesulfonyl chloride 6.14 g (0.03 mol). TLC monitors reaction, evaporates to dryness after reaction finishes ( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives.

[0065] (2 pairs( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives are separated and detected using the following different chromatographic conditions

[0066] A. Will( R )-(+)-1-phenylethanesulfonyl chloride and ( RS )-3-aminopiperidine derivatives are dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography. Liquid chromatography conditions: Dima C18 chromatographic column, mobile phase is water-methanol (volume ratio 30:70), UV detection wavelength is 2...

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Abstract

The invention belongs to the technical field of medicine analysis and particularly relates to a determination method of an excessive rate of 3-aminopiperidine enantiomer. The determination method takes (R)-(+)-1-phenylethyl sulfonyl chloride as a derivatization reagent to be subjected to a rapid single-derivatization reaction with 3-aminopiperidine; and then a common reversed-phase HPLC-UV (High Performance Liquid Chromatography-Ultraviolet) is used for carrying out qualitative and quantitative analysis on (R)-(+)-1-phenylethyl sulfonyl chloride-3-aminopiperidine, and determining the excessive rate of enantiomer. The method has the advantages of simplicity in operation, rapidness, good repeatability, high sensitivity and easiness in standardized operation.

Description

technical field [0001] The invention belongs to the technical field of drug analysis, in particular to a method for determining the excess rate of 3-aminopiperidine enantiomers. Background technique [0002] Although there are two nitrogen atoms in the molecular structure of 3-aminopiperidine, due to the low energy of the lone pair of electrons of the nitrogen atom, 3-aminopiperidine has almost no absorption in the ultraviolet region. -Aminopiperidine becomes weak for accurate and reliable characterization and quantification. [0003] Wang Canhui et al. (CN103435538 ​​B) used tert-butoxycarbonyl to replace the 1 and 3 nitrogens of 3-aminopiperidine respectively, and analyzed it at 215nm with chiralpark AD-H 4.6×250 chiral chromatographic column, and the mobile phase was n-hexane alkanes, the flow rate is 1.0 mL / min, and the peak time has not been reported. Meek et al. (WO2011160037) used a CrownpakTM CR+ (150×4.6mm) chiral column and a differential refractive index detecto...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/89G01N30/74
CPCG01N30/74G01N30/89
Inventor 孙凤霞白少玲孔飞飞孔琳张琛韩珊
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY