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Method for preparing 2-para octylphenyl ehtyl-2-amino propanediol

A technology of aminopropanediol and octylphenethyl, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems of labor protection, high price, low yield, etc., and achieve low price. Effect

Inactive Publication Date: 2004-09-15
马启明
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the reaction steps are long, and the yields including steps such as Friedel-Crafts reaction, reduction, hydrolysis, and refining are relatively low, so that the total yield is only about 4%.
However, the price of octylbenzene as a starting material is high, so that the cost of the product is also high
In addition, the intermediate with the structure of α-bromoacetophenone has lachrymatory effect, and there are labor protection problems

Method used

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  • Method for preparing 2-para octylphenyl ehtyl-2-amino propanediol
  • Method for preparing 2-para octylphenyl ehtyl-2-amino propanediol
  • Method for preparing 2-para octylphenyl ehtyl-2-amino propanediol

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Embodiment

[0046] One. The preparation of compound p-octanoyl chloride ethylbenzene (III):

[0047] Under the cooling of cooling water, after putting 365.6g (2.25mol) of octanoyl chloride into the reactor, control the inner temperature not to exceed 50°C and put in 118g of anhydrous aluminum trichloride in batches, stir for 30 minutes after adding, and cool the temperature with ice-salt water. At -2°C, 140.5 g (1 mol) of chloroethylbenzene (II) was slowly added dropwise. After the addition, keep warm for 4 hours, pour into hydrochloric acid for hydrolysis, extract twice with chloroform, and combine the chloroform layers. The organic layer was washed twice with 10% hydrochloric acid, the chloroform layer was separated, washed with saturated brine until neutral, dried with anhydrous sodium sulfate, and concentrated to obtain about 252 g of p-octanoyl chloride ethylbenzene (III) as a red oil. The rate is 94%.

[0048] 1 H NMR (CDCl 3 )δ: 7.89(d, J=9.6Hz, 2H), 7.26(d, J=9.6Hz, 2H), 4.15~...

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Abstract

The invention provides a method to prepare a compound method, including the steps: ethylbenzene and capryl chloride make Friedel-Crafts reaction to generate p-capryl chloroethylbenzene; convert capryl chloroethylbenzene under the action of sodium iodide into p-capryl iodoethylbenzene; p-capryl iodoethylbenzene and acetylamino diethyl malonate condense under the action of alkali to generate 2-(p-capryl phenethyl)-2-acetylamino diethyl malonate; or p-capryl iodoethylbenzene makes elimination reaction under the action of alkali to generate p-capryl styrene, which together with acetylamino diethyl malonate condenses under the action of alkali into 2-(p-capryl phenethyl)-2- acetylamino diethyl malonate; a compound is reduced into 2-[4-(1-hydroxyoctyl) phenethyl-]2- acetylamino propylene alcohol; the other coumpound makes hydrogenolysis to obtain 2-(p-octyl phenethyl)-acetylamino propylene alcohol; make alkali hydrolyzation and then acidifies them into salt, so as to obtain it. It also provides a method to prepare intermediate in the above preparing course.

Description

Technical field [0001] The invention relates to a method for preparing 2-p-octylphenethyl-2-aminopropanediol. Background technique [0002] 2-p-octylphenethyl-2-aminopropanediol (FTY720 for short) and its hydrochloride are immunosuppressants and are currently undergoing clinical research. The pharmacological test results show that the compound can prolong the survival period of animals in the experiments of rat skin transplantation, heart transplantation and dog kidney transplantation. In particular, the combination of FTY-720 and cyclosporine and other immunosuppressants can more significantly inhibit the immune rejection of transplanted organs and prolong the survival of animals than using cyclosporin or FTY-720 alone. Moreover, the toxicity of this compound is significantly lower than that of immunosuppressants currently used clinically, and it will have a good prospect. [0003] The structural formula of 2-p-octylphenethyl-2-aminopropanediol hydrochloride (I) is shown ...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C215/28
Inventor 马启明
Owner 马启明
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