Method for preparing berberine hydrochloride intermittent

A technology for berberine hydrochloride and intermediates, which is applied in the field of preparation of berberine hydrochloride intermediates, can solve the problems of unsuitability for industrialized production, high cost of sodium borohydride, and complicated post-processing processes, and achieves convenient industrialized production and catalytic performance. The effect of high activity and selectivity and low catalyst dosage

Inactive Publication Date: 2018-04-03
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The cost of sodium borohydride is high, the post-treatment process is cumbersome, and it needs to use dangerous ether as a solvent, which is not suitable for industrial production
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Method used

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  • Method for preparing berberine hydrochloride intermittent
  • Method for preparing berberine hydrochloride intermittent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add the ethanol solution of 2,3-dimethoxybenzaldehyde piperonyl ethylamine (which contains 200g of 2,3-dimethoxybenzaldehyde piperonyl ethylamine), 1.6g of isopropylamine and 100g of hydrazine hydrate aqueous solution into the reaction flask . React at 50-65°C for 4h. Cool down, concentrate to dryness under reduced pressure, add hydrogen chloride / ethanol solution dropwise to pH 4~5, cool down to below 0°C, crystallize, filter, and dry to obtain N-2',3'-dimethoxybenzylpiperylethylamine Hydrochloride 204g, yield 96.4%, melting point 144.3-145.2°C, HPLC purity 99.1%.

Embodiment 2

[0027] Add 2,3-dimethoxybenzaldehyde piperonyl ethylamine ethanol solution (which contains 2,3-dimethoxybenzaldehyde piperonyl ethylamine 200g), 1g isopropylamine and 120g hydrazine hydrate aqueous solution into the reaction flask. React at 65-75°C for 5h. Cool down, concentrate to dryness under reduced pressure, add hydrogen chloride / ethanol solution dropwise to pH 4~5, cool down to below 0°C, crystallize, filter, and dry to obtain N-2',3'-dimethoxybenzylpiperylethylamine Hydrochloride 203g, yield 95.9%, melting point 144.5-145.6°C, HPLC purity 99.0%.

Embodiment 3

[0029] Add 2,3-dimethoxybenzaldehyde piperonyl ethylamine ethanol solution (which contains 2,3-dimethoxybenzaldehyde piperonyl ethylamine 200g), 2.4g isopropylamine and 60g hydrazine hydrate aqueous solution into the reaction flask . React at 30-40°C for 5h. Cool down, concentrate to dryness under reduced pressure, add hydrogen chloride / ethanol solution dropwise to pH 4~5, cool down to below 0°C, crystallize, filter, and dry to obtain N-2',3'-dimethoxybenzylpiperylethylamine Hydrochloride 206g, yield 97.3%, melting point 144.3-145.4°C, HPLC purity 99.2%.

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PUM

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Abstract

The invention discloses a method for preparing a berberine hydrochloride intermittent. The method comprises the following steps: performing a reduction reaction on an ethanol solution of 2,3-dimethoxybenzaldehyde polycondensed homopiperony lamine (II) and a hydrazine hydrate solution under catalysis of isopropamide, thereby obtaining N-2',3'-dimethoxybenzyl homopiperony lamine (I). Compared witha conventional synthesis method, the method has the advantages of being simple and convenient in synthesis method, high in catalysis activity, easy in product separation and purification, high in product purity, high in yield, small in potential safety hazard, applicable to industrial production, and the like.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and relates to a preparation method of a berberine hydrochloride intermediate. Background technique [0002] Berberine hydrochloride, also known as berberine hydrochloride, chemical name: 5,6-dihydro-9,10-dimethoxybenzo[g]-l,3-benzodioxolane[5,6- α]Quinazine hydrochloride dihydrate, molecular formula: C 20 h 18 ClNO 4 • 2H 2 0, the structural formula is: [0003] [0004] Berberine hydrochloride is an isoquinoline alkaloid that exists in plants and can be extracted from a variety of plants, such as Coptis chinensis, Phellodendron cork, Three needles, Barberry, Celandine, Nandina, Berberis, Tiepilian Wait. Berberine hydrochloride is a broad-spectrum antibacterial drug, widely used clinically to treat tuberculosis, diarrhea, dysentery, and enteritis. [0005] In recent years, a large number of studies and clinical applications have shown that berberine hydrochlorid...

Claims

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Application Information

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IPC IPC(8): C07D317/58
CPCC07D317/58
Inventor 冯旋付林赵成安
Owner HUAZHONG PHARMA
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