Preparation method of posaconazole intermediate 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine

A technology of aminophenyl and posaconazole, which is applied in organic chemistry and other fields, can solve problems such as strict equipment requirements, safety risks, and difficult reaction operations, and achieve the effects of reduced product costs, high yields, and low prices
CN111362886AActive Publication Date: 2020-07-03四川澄华生物科技有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
四川澄华生物科技有限公司
Publication Date
2020-07-03

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Abstract

The invention discloses a preparation method of a posaconazole intermediate, namely 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine, belonging to the field of medicinal chemistry. The preparation method comprises the following steps: S1, with chlorobromobenzene and anhydrous piperazine as raw materials, generating 1,4-bis(4-chlorophenyl)piperazine under certain conditions; S2, performing single-side methylation on the product generated in the step S1 to obtain 1-(4-methoxyphenyl)-4-(4-chlorophenyl)piperazine; S3, performing ammoniation on the product in the step S2 to obtain 1-(4-methoxyphenyl)-4-(4-aminophenyl)piperazine; and S4, demethylating the product obtained in the step S3, and carrying out crystallizing and purifying to obtain the 1-(4-aminophenyl)-4-(4-hydroxylphenyl)piperazine.The raw materials used in the preparation method are very cheap; reaction conditions are relatively simple; the method is easy to implement; yield is high; and the cost of a final product can be obviously reduced.
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Description

technical field

[0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of a posaconazole intermediate 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine. Background technique

[0002] Posaconazole is a derivative of itraconazole, a second-generation triazole antifungal drug that was listed on the US FDA in 2006, and is widely used in patients with an increased risk of infection due to severe immunodeficiency. Posaconazole (chemical name: 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-tri Azol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3 -base]-1,2,4-triazol-3-one), the structural formula is:

[0003]

[0004] 1-(4-aminophenyl)-4-(4-hydroxyphenyl)piperazine is one of the important intermediates for the synthesis of posaconazole API, molecular formula C 16 h 19 N 3 O, molecular weight 269.34, structural formula is

[0005] According to the records of patent U...

Claims

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