Preparation method and application of 6-benzylphenethylamine derivatized β-cyclodextrin bonded SBA-15

A technology of benzylphenethylamine and cyclodextrin is applied in the field of preparation of chiral stationary phases, which can solve the problems of affecting chiral separation effect, inter-batch chromatographic separation performance of difficult chiral stationary phases, and cyclodextrin port congestion. , to improve the chiral separation ability and range, improve the chiral recognition effect, and reduce the mass transfer resistance.

Inactive Publication Date: 2017-02-22
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, cyclodextrin derivatization methods mainly include methylation, acetylation, benzoylation, phenylcarbamate, etc., and most of them are full derivatization or partial derivatization. Due to the uncertainty of degree of substitution or position , it is difficult to ensure and effectively control the batch-to-batch chromatographic separation performance of the prepared chiral stationary phase, and the full derivatization sometimes causes the congestion of the cyclodextrin port, which affects the chiral separation effect
The chiral stationary phase of monosubstituted benzylphenethylamine derivatized β-cyclodextrin has not been reported yet

Method used

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  • Preparation method and application of 6-benzylphenethylamine derivatized β-cyclodextrin bonded SBA-15
  • Preparation method and application of 6-benzylphenethylamine derivatized β-cyclodextrin bonded SBA-15
  • Preparation method and application of 6-benzylphenethylamine derivatized β-cyclodextrin bonded SBA-15

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Take SBA-15 (400m 2 / g) Activated silica gel 2.5g as the base.

[0034] 1) Under a nitrogen atmosphere, use anhydrous N,N-dimethylformamide as a solvent to sulfonylate β-cyclodextrin (mmol) with 6-p-toluene: N-benzyl-1-phenylethylamine ( ml) at a ratio of 1.0:0.6, add 6-p-toluenesulfonylated β-cyclodextrin and N-benzyl-1-phenylethylamine into a round bottom flask, stir for 1 hour to fully dissolve the raw materials to form a homogeneous solution ; Configure a condenser tube and a calcium chloride drying tube, under the protection of nitrogen, in an 80 ° C oil bath, magnetically stir the reaction for 4 hours; then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, and add acetone- Aqueous solution (10:1, v / v), collect the white precipitate, and repeat the above operation 3 times, after drying in a vacuum oven at 50°C, 6-benzylphenethylamine β-cyclodextrin is obtained, and the reaction yield of this step is 60%;

[0035] 2)...

Embodiment 2

[0042] Take SBA-15 (500m 2 / g) Activated silica gel 2.5g as the base

[0043] 1) Under a nitrogen atmosphere, using anhydrous N,N-dimethylformamide as a solvent, according to 6-p-toluenesulfonylation of β-cyclodextrin (mmol): N-benzyl-1-phenylethylamine ( ml) at a ratio of 1.0:1.0, add 6-p-toluenesulfonylated β-cyclodextrin and N-benzyl-1-phenylethylamine into a round bottom flask, stir for 2 hours to fully dissolve the raw materials to form a homogeneous solution ; configure a condenser tube and a calcium chloride drying tube, under the protection of nitrogen, in an 85 ° C oil bath, magnetically stir the reaction for 6 hours; then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, and add acetone- aqueous solution (10:1, v / v), collect the white precipitate, and repeat the above operation 3 times, after drying in a vacuum oven at 50°C, 6-benzylphenethylamine β-cyclodextrin is obtained, and the reaction yield of this step is 68%; ...

Embodiment 3

[0051] Take SBA-15 (420m 2 / g) Activated silica gel 2.5g as the base.

[0052] 1) Under a nitrogen atmosphere, using anhydrous N,N-dimethylformamide as a solvent, according to 6-p-toluenesulfonylation of β-cyclodextrin (mmol): N-benzyl-1-phenylethylamine ( ml) at a ratio of 1.0:0.8, add 6-p-toluenesulfonylated β-cyclodextrin and N-benzyl-1-phenylethylamine into a round bottom flask, stir for 1.5h to fully dissolve the raw materials to form a homogeneous phase solution; equipped with a condenser tube and a calcium chloride drying tube, under the protection of nitrogen, in an oil bath at 85°C, and reacted with magnetic stirring for 5 hours. Then evaporate the solvent under reduced pressure, dissolve the solid in a small amount of hot water, add acetone-water solution (10:1, v / v) with stirring, collect the white precipitate, and repeat the above operation 3 times, and dry in a vacuum oven at 50°C Finally, 6-benzylphenethylamine β-cyclodextrin was obtained, and the reaction yiel...

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Abstract

The invention discloses a preparation method of 6-benzyl phenylethylamine derivative beta-cyclodextrin bonded SBA-15. The preparation method comprises the following steps: with 6-p-tolylsulfonyl beta-cyclodextrin and N-benzyl-1-phenylethylamine as raw materials, preparing a 6-benzyl phenylethylamine derivative beta-cyclodextrin ligand; adding a coupling agent 3-isocyanate propyl siloxane, and reacting to prepare siloxane containing the 6-benzyl phenylethylamine derivative beta-cyclodextrin; with an ordered mesoporous SBA-15 silica gel as a bonding matrix, reacting the bonding matrix with the siloxane containing the 6-benzyl phenylethylamine derivative beta-cyclodextrin to obtain a coarse product of 6-benzyl phenylethylamine derivative beta-cyclodextrin bonded SBA-15; with acetone as a solvent, extracting and purifying via a soxhlet to prepare the 6-benzyl phenylethylamine derivative beta-cyclodextrin bonded SBA-15. The preparation method disclosed by the invention is simple and the convenient, the cost is lower, the adaptability is wide, the stereoselectivity is stronger, meanwhile the permeability is good, the mass transfer resistance is small, and the 6-benzyl phenylethylamine derivative beta-cyclodextrin bonded SBA-15 can be used as a stationary phase in chiral chromatography for the chiral separation and analysis of high performance Liquid chromatography.

Description

technical field [0001] The invention relates to a preparation method of a chiral stationary phase, in particular to a preparation method and application of 6-benzylphenethylamine derivatized β-cyclodextrin bonded SBA-15. Background technique [0002] The life system is a complex chiral system. For example, proteins, biological enzymes, polysaccharides, DNA, etc. all have chirality. There are often significant differences in activity, toxicity and pharmacokinetics. β-blockers are the most common chiral drugs for the clinical treatment of hypertension, angina pectoris, arrhythmia and other diseases. Animal experiments have shown that the (S)-enantiomer of most β-blockers is usually 50 to 500 times more active than the (R)-enantiomer. For example, the most commonly used propranolol hydrochloride has about 100 times stronger S-type than R-type enantiomer in terms of β-receptor blocking effect, and (R)-type enantiomer will inhibit libido, so it is a male contraceptive Drugs, l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16B01J20/29B01J20/30B01D15/22
Inventor 李来生程彪平周仁丹李良张宏福曹志刚曾春
Owner NANCHANG UNIV
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