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HPLC (high performance liquid chromatography) analyzing method for 3-aminopiperidine

An aminopiperidine and analytical method technology, applied in the field of pharmaceutical analysis, can solve problems such as powerlessness and large sample volume requirements, and achieve the effects of simple operation, good reproducibility, and convenient standardized operation

Active Publication Date: 2014-08-27
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • 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 electrons of the nitrogen atom, 3-aminopiperidine has almost no absorption in the ultraviolet region, so the traditional HPLC-UV method is accurate and reliable The qualitative and quantitative methods for 3-aminopiperidine become weak
But in fact, the differential refractive index detector requires a large amount of sample to be analyzed.

Method used

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  • HPLC (high performance liquid chromatography) analyzing method for 3-aminopiperidine
  • HPLC (high performance liquid chromatography) analyzing method for 3-aminopiperidine
  • HPLC (high performance liquid chromatography) analyzing method for 3-aminopiperidine

Examples

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Effect test

Embodiment 1

[0037] Example 1 : Analysis of 3-Aminopiperidine by Reversed-Phase High Performance Liquid Chromatography

[0038] (1) Reverse-phase high-performance liquid chromatography analysis of (RS)-3-aminopiperidine

[0039] Weigh 2.9 g (0.029 mol) of (RS)-3-aminopiperidine, dissolve it in 40 mL of petroleum ether, stir at 40°C, and slowly add 16.4 g (0.116 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and the solvent was evaporated to dryness after the reaction to obtain (RS)-dibenzoyl-3-aminopiperidine.

[0040] (RS)-dibenzoyl-3-aminopiperidine was dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography. Liquid chromatography conditions: Dima C18 column, the mobile phase is water-methanol (40:60), the UV detection wavelength is 254nm, the flow rate is 0.8 mL / min, the column temperature is 30°C, and the injection volume is 20 μL. The retention time is shown in the following table 1, and its spectrum is shown in f...

Embodiment 2

[0048] Example 2 : Chiral purity analysis of (RS)-3-aminopiperidine

[0049] Weigh 2.9 g (0.029 mol) of (RS)-3-aminopiperidine, dissolve it in 40 mL of hexane, stir at 40°C, and slowly add 16.4 g (0.116 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and the solvent was evaporated to dryness after the reaction to obtain (RS)-dibenzoyl-3-aminopiperidine.

[0050] (RS)-dibenzoyl-3-aminopiperidine was dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography.

[0051] (1) Liquid chromatography condition A: ChromTech CHIRAL-AGP column, mobile phase is 0.015 mol / L phosphate aqueous solution-acetonitrile (92:8), UV detection wavelength is 254nm, flow rate is 0.8 mL / min, column temperature is 30°C, the injection volume is 20 μL. Retention time, resolution and chiral purity are shown in Table 2 below, and the spectrum is shown in figure 2 .

[0052] (2) Liquid chromatography condition B: ChromTech CHIRAL-AGP column,...

Embodiment 3

[0055] Example 3 : The chiral purity analysis of (R)-3-aminopiperidine test sample

[0056] Weigh 2.9 g (0.029 mol) of the (R)-3-aminopiperidine test sample, dissolve it in 40 mL of dichloromethane, stir at 38°C, and slowly add 16.4 g (0.116 mol) of benzoyl chloride dropwise. The reaction was monitored by TLC, and the solvent was evaporated to dryness after the reaction to obtain (R)-dibenzoyl-3-aminopiperidine.

[0057] (R)-dibenzoyl-3-aminopiperidine is dissolved in mobile phase and then detected and analyzed by high performance liquid chromatography.

[0058] (1) Liquid chromatography condition A: ChromTech CHIRAL-AGP chromatographic column, the mobile phase is 0.02 mol / L phosphate aqueous solution-acetonitrile (92:8), the ultraviolet detection wavelength is 254nm, the flow rate is 0.8 mL / min, and the column temperature is 30°C, the injection volume is 20 μL. The peak area percentage and chiral purity are shown in Table 3 below, and the enlarged view of the liquid chrom...

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Abstract

The invention belongs to the technical field of medicament analysis, and particularly relates to a qualitative and quantitative method of 3-aminopiperidine as well as a detection method of chiral purity of 3-aminopiperidine. According to the invention, excessive benzoyl chloride is adopted as a derivatization reagent to be subjected to rapid bi-derivatization reaction with 3-aminopiperidine so as to generate diphenyl 3-aminopiperidine, and then common phase reversal HPLC-UV(high performance liquid chromatography-ultraviolet) is used for analyzing diphenyl 3-aminopiperidine qualitatively and quantitatively; Chiral HPLC Columns taking glycoprotein as a filling are adopted for determining the enantiomeric excess rate of diphenyl 3-aminopiperidine. The method is simple and rapid to operate, is good in reproducibility, is high in flexibility, and 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] Although there are two nitrogen atoms in the molecular structure of 3-aminopiperidine, due to the low energy of the lone pair electrons of the nitrogen atom, 3-aminopiperidine has almost no absorption in the ultraviolet region, so the traditional HPLC-UV method is accurate and reliable The qualitative and quantitative methods for 3-aminopiperidine become weak. 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 95:5 (V:V) HClO 4 (pH=1): MeOH, column temperature 0°C, flow rate 0.6 mL / min, (S)-3-aminopiperidine elutes in 3.0 minutes, and (R)-3-aminopiperidine elutes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02
Inventor 孙凤霞王美玲孔琳张凤娇孔飞飞贾琳茹
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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