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Process of synthesizing fexofenadine intermediate

A synthesis method and ligand technology, applied in the field of synthesis of fexofenadine intermediates, can solve problems such as high pressure on environmental governance, harmful to human body, difficult to recycle, etc., and achieve low environmental pollution, short reaction cycle and high product quality. Good results

Inactive Publication Date: 2007-06-27
HANGZHOU NORMAL UNIVERSITY +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the method uses a large amount of HgO, which is harmful to the human body and difficult to recycle and treat, the pressure on environmental governance in the production process is still relatively large.

Method used

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  • Process of synthesizing fexofenadine intermediate
  • Process of synthesizing fexofenadine intermediate
  • Process of synthesizing fexofenadine intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: 4-[4-[4-(hydroxyl diphenylmethyl)-1-piperidinyl]-butenyl]-α, the synthesis of α-dimethylphenylacetic acid methyl ester

[0042] Its reaction equation is:

[0043]

[0044] 4.45g (495g / mol, 8.99mmol) starting material (IV), 300ml ethanol, 0.38g 5%Pd / CaCO 3 successively added to a 500ml three-necked flask. After stirring at room temperature, 20 drops of quinoline (about 1 ml) were added dropwise. Stirring was stopped, and the air in the system was replaced with nitrogen for 3 times, and hydrogen for 1 time. Keep the hydrogen pressure at 0.02MPa, stir and react at 30°C for 10h, stop the reaction, vent, filter, concentrate and refine to obtain 4.02g of product (V). The conversion rate reaches 90%. 1 H NMR (CDCl 3 ): 7.1~7.5(aromatics, 14H), 6.40(d, 1H), 5.60(m, 1H), 3.63(s, 3H), 2.95(d, 2H), 2.41~2.52(m, 5H), 1.94~ 1.98 (m, 2H), 1.56 (s, 6H), 1.46~1.51 (m, 4H).

Embodiment 2

[0045] Example 2: (±)-4-[1-hydroxyl-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-a,a-dimethylphenylacetic acid methyl Synthesis of esters

[0046] Its reaction equation is:

[0047]

[0048] Compound (V) 4.02g (497g / mol, 8.09mmol), manganese acetate (0.64mmol), Schiff base ligand (0.64mmol) and NaBH 4 (16.18mmol) was added 150ml of mixed solvent of toluene and ethanol (1:1), at room temperature and normal pressure, stirred and introduced oxygen to react for 4 hours, followed by dot plate tracking, after the reaction of the reactants was complete, the ethanol was removed under reduced pressure, and the organic mixture was washed with water. phase, the organic phase was dried with magnesium sulfate, filtered and the filtrate was taken, and the solvent was removed to obtain a crude product. 3.65 g of the target product (I) was obtained by column separation with a yield of 90%. 1 H NMR (CDCl 3 ): 7.1~7.5(aromatics, 14H), 4.59(d, 1H), 3.15(d, 1H), 2.98(d, 1H), 2.40~2.5...

Embodiment 3

[0050] The reaction solvent was changed to methanol, and the others were the same as in Example 1 to obtain 3.98 g of product (V) (yield 89%).

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Abstract

The present invention is process of synthesizing fexofenadine intermediate (+ / -)-4-[1-hydroxy-4-[4-(hydroxyl dipenyl methyl)-1-piperidino]-butyl]-alpha, alpha-dimethyl phenylacetate. The process includes catalytic hydrogenation reaction, addition reaction, and product separating purification. The process has atomic utilization rate of 100 %, facile cheap material, high operation safety, short reaction period, high yield, high product quality and less environmental pollution, and is suitable for industrial production.

Description

(1) Technical field [0001] The present invention relates to an intermediate of fexofenadine: (±)-4-[1-hydroxyl-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α, Synthetic method of α-dimethylphenylacetate. (2) Background technology [0002] (±)-4-[1-Hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethylphenylacetic acid hydrochloride, Also known as Fexofenadine (Fexofenadine), has a good antihistamine H 1 Receptor action, without sedative side effects, is an ideal class of third-generation antihistamines. It is derived from the key intermediate of fexofenadine (±)-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α -Dimethylphenylacetate can be obtained by hydrolysis under alkaline conditions. [0003] In the prior art, about (±)-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethylbenzene Acetate (I) or (±)-4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethyl The chemical synthesis met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22
Inventor 章鹏飞顾海宁汪劲松张习坤李小玲沈超
Owner HANGZHOU NORMAL UNIVERSITY
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