HPLC (High Performance Liquid Chromatography) analysis method for 3-aminopiperidine

A technology of aminopiperidine and analysis method, applied in high performance liquid chromatography analysis of quantitative method and its chiral purity, and qualitative field of 3-aminopiperidine, which can solve the problems of long peak time and achieve high sensitivity and reproducibility Good performance, easy to standardize the effect of operation

Active Publication Date: 2014-09-10
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the peak time is long, and it takes

Method used

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  • HPLC (High Performance Liquid Chromatography) analysis method for 3-aminopiperidine
  • HPLC (High Performance Liquid Chromatography) analysis method for 3-aminopiperidine
  • HPLC (High Performance Liquid Chromatography) analysis method for 3-aminopiperidine

Examples

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Embodiment 1

[0041] Example 1 Analysis of 3-Aminopiperidine by Reversed-Phase High Performance Liquid Chromatography

[0042] (1) Reverse-phase high-performance liquid chromatography analysis of (RS)-3-aminopiperidine

[0043] Weigh 2.9 g (0.029 mol) of (RS)-3-aminopiperidine, dissolve it in 150 mL of dichloromethane, stir at 5°C, and slowly add 4.1 g (0.029 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and evaporated to dryness after the reaction was completed to obtain (RS)-benzoyl-3-aminopiperidine.

[0044](RS)-benzoyl-3-aminopiperidine was dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography. Liquid chromatography conditions: Dima C18 chromatographic column, mobile phase is 0.01mol / L phosphate aqueous solution-methanol (90:10), UV detection wavelength is 254nm, flow rate is 1.0mL / min, column temperature is 30°C, sample injection Volume 20 μL. The retention time is shown in the following table 1, and its spectr...

Embodiment 2

[0052] Example 2 Analysis of chiral purity of (RS)-3-aminopiperidine

[0053] Weigh 2.9 g (0.029 mol) of (RS)-3-aminopiperidine, dissolve it in 150 mL of petroleum ether, stir at 3°C, and slowly add 4.1 g (0.029 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and evaporated to dryness after the reaction was completed to obtain (RS)-benzoyl-3-aminopiperidine.

[0054] (RS)-benzoyl-3-aminopiperidine was dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography.

[0055] (1) Liquid chromatography condition A: ChromTech CHIRAL-AGP column, the mobile phase is 0.015mol / L phosphate aqueous solution-isopropanol (99:1), the UV detection wavelength is 254nm, the flow rate is 0.8 mL / min, the column The temperature was 30°C, and the injection volume was 20 μL. Retention time, resolution and chiral purity are shown in Table 2 below, and the spectrum is shown in figure 2 .

[0056] (2) Liquid chromatography condition B: ...

Embodiment 3

[0059] Example 3 : Chiral purity analysis of (R)-3-aminopiperidine

[0060] Weigh 2.9 g (0.029 mol) of (R)-3-aminopiperidine, dissolve it in 150 mL of dichloromethane, stir at 5°C, and slowly add 4.1 g (0.029 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and evaporated to dryness after the reaction was completed to obtain (R)-benzoyl-3-aminopiperidine.

[0061] (1) Liquid chromatography condition A: ChromTech CHIRAL-AGP chromatographic column, the mobile phase is 0.015mol / L phosphate aqueous solution-isopropanol (99:1), the ultraviolet detection wavelength is 254nm, the flow rate is 0.8 mL / min, the column The temperature was 30°C, and the injection volume was 20 μL. The peak area percentage and chiral purity are shown in Table 3 below, and its liquid chromatogram is shown in image 3 .

[0062] (2) Liquid chromatography condition B: ChromTech CHIRAL-AGP chromatographic column, the mobile phase is 0.015mol / L phosphate aqueous solution-methanol (97:3...

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Abstract

The invention belongs to the technical field of medicine analysis and particularly relates to a quantitative method for 3-aminopiperidine and a detection method for the chiral purity of 3-aminopiperidine. According to the method, benzoyl chloride which is used as a derivatization reagent and 3-aminopiperidine are rapidly derived at a low temperature in a large quantity of organic solvents to generate benzoyl-3-aminopiperidine; then a detection analysis of benzoyl-3-aminopiperidine is carried out by using HPLC-UV (High Performance Liquid Chromatography-Ultraviolet). The method carries out qualitative analysis and quantitative analysis by adopting a common C18 column, and carries out enantiomeric excess rate determination by adopting a chiral chromatographic column. The method is simple to operate, high in sensitivity and high in accuracy, is easy for standardized operation.

Description

technical field [0001] The invention belongs to the technical field of drug analysis, and in particular relates to a qualitative and quantitative method for 3-aminopiperidine and a high-performance liquid chromatography analysis method for its chiral purity. Background technique [0002] 3-aminopiperidine is an important intermediate of linagliptin, establish and confirm the qualitative and quantitative methods and chirality of 3-aminopiperidine ee The value determination method is of great significance to the detection and monitoring of 3-aminopiperidine. The HPLC detection method has the advantages of high detection sensitivity, high precision, less time required for detection, and high repeatability of detection results. It is a commonly used detection method in current analytical chemistry. Meek et al. (WO2011160037) adopted Crownpak TM CR+ (150×4.6 mm) chiral column, differential refractive index detector directly detects 3-aminopiperidine, and its mobile phase is 95...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 孙凤霞郝忠翠郝飞飞王美玲张凤娇
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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