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Preparation method of 4-benzylpiperazine ethylimide (iminomethylbenzene) hydrazine compound

A compound and solvate technology, which is applied in the field of synthesis of 4-benzylpiperazine ethyleneimide hydrazide compounds for the treatment of tumors, and can solve problems such as difficulty in purchasing

Active Publication Date: 2011-12-14
DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method has a short route, because the reagent anhydrous hydrazine is used in the reaction, the reagent is highly toxic and dangerous, and it is difficult to purchase

Method used

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  • Preparation method of 4-benzylpiperazine ethylimide (iminomethylbenzene) hydrazine compound
  • Preparation method of 4-benzylpiperazine ethylimide (iminomethylbenzene) hydrazine compound
  • Preparation method of 4-benzylpiperazine ethylimide (iminomethylbenzene) hydrazine compound

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Embodiment 1

[0057] The synthesis of embodiment 1.4-benzyl piperidine acyl (N-amino iminomethyl-3-hydroxyl phenyl) hydrazine

[0058]

[0059] (1), the preparation of ethyl 2-chloroacetylide hydrochloride:

[0060] In an ice bath, under magnetic stirring, 10 g (130 mmol) of chloroacetonitrile and 6.1 g (130 mmol) of absolute ethanol were dissolved in 100 ml of absolute ether, and dry hydrogen chloride gas was introduced into the reaction solution, and after about 40 minutes A large amount of white solids were precipitated, and the solids were filtered out, washed three times with anhydrous ether, and dried to obtain 16 g of ethyl 2-chloroacetimide hydrochloride, with a yield of 98% and a melting point of 84-86°C. Proton spectrum (400MHz, DMSO): 4.40(s, 2H); 4.20(q, 2H); 1.24(t, 3H).

[0061] (2), the preparation of 2-allyl-6-(N-aminoiminomethyl)phenol:

[0062] At room temperature, under magnetic stirring, add 15ml of methanol, 14.7g (250mmol) of 85% hydrazine hydrate solution in ...

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Abstract

The invention relates to a preparation method of 4-benzyl piperazi ethyliminumacyl (formimidoyl benzol) hydrazine compounds, and specifically relates to a method for preparing a compound of the following formula I or its pharmaceutically acceptable salts or solvates, wherein, R1, R2, R3 and R4 are respectively selected from hydrogen atom, hydroxyl, halogen, C1-8 alkenyl, C1-8 alkyl and sulfonamido. The method comprises the step of: (1) in a suitable organic solvent, reacting hydrazine hydrate with the compound of formula 1a so as to obtain the compound of formula 1b; (2) with the existence of alkali, reacting 2-chloracetyl iminoiacetate hydrochloride with the compound of formula 1b in a suitable organic solvent so as to generate the compound of formula 1c; (3) in the presence of alkali and in a proper organic solvent, reacting the compound of formula 1c with the compound of formula 1d, thus obtaining the compound of formula I. The method of the invention is characterized by security, simplicity and convenient operation.

Description

technical field [0001] The invention relates to a novel method for synthesizing a class of 4-benzylpiperazine ethylimidyl (iminomethylbenzene) hydrazine compounds for treating tumors. Background technique [0002] 4-Benzylpiperazine ethylimidyl (iminomethylphenyl) hydrazine compounds have been proved to be a class of molecules with obvious anti-tumor activity both in vivo and in vitro, and have little toxic side effects on normal cells. For details, see Another Chinese patent application CN2008100094484 of the applicant. Therefore, the development of such compounds has very important practical value. [0003] At present, there are relatively few synthetic route reports in the literature. The existing route is to first synthesize 2-chloroacetylene ethyl ester hydrochloride with 2-chloroacetonitrile as a raw material, and then react with 1-benzylpiperazine to generate 4-benzylpiperazine Linimidoyl ethyl ester, and finally use a one-pot method to get the final product. Altho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/15A61P35/00
Inventor 钟宪斌程笠人谭孟群马志珂
Owner DONGGUAN ZHENGXING BEITE MEDICINE TECH CO LTD
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