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Method for preparing 4-(piperidine-3-yl)aniline

A technology of piperidine and aniline, which is applied in the field of preparation of 4-aniline, an intermediate of anticancer drug nirapabib, can solve the problems of low cost, difficult purification of by-products, and high yield, and achieves reduced production cost and good yield. , mild conditions

Inactive Publication Date: 2017-02-22
QINGDAO YUNTIAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The object of the present invention is to overcome defects such as existing 4-(piperidin-3-yl) aniline preparation method to use precious metal cost high, many by-products are difficult to purify etc., provide a kind of new preparation 4-(piperidin-3-yl)aniline 3-base) the method of aniline, this method avoids the one-time reduction of nitro group and pyridine to obtain the target product using precious metals, the cost is low, the yield is high and the reaction will not generate such as N-(4-(pyridin-3-yl) A by-product of phenyl) hydroxylamine, the post-processing is more convenient

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0024] N-allyl-3-(4-nitrophenyl)pyridine quaternary ammonium salt

[0025] 20g (100mmol) of 3-(4-nitrophenyl)pyridine and 1.3g (20mmol) of zinc powder were added to a reaction vessel containing 100ml of acetonitrile, then 13.3g (110mmol) of 3-bromopropene was added at 65°C, React for 2 hours, filter, wash the filter cake three times with acetonitrile, combine the filtrate washings, concentrate, then recrystallize from petroleum ether, and dry in vacuo to obtain N-allyl-3-(4-nitrophenyl)pyridinium quaternary ammonium salt 31.4 g, yield 97.7%. HRMS (ESI + )m / z Calculated C 18 h 16 N 2 o 2 (M-Br) + 242.1037, Found 242.1045.

Embodiment 2

[0027] N-allyl-3-(4-nitrophenyl)pyridine quaternary ammonium salt

[0028] 20g (100mmol) of 3-(4-nitrophenyl)pyridine and 1.95g (30mmol) of zinc powder were added to a reaction vessel containing 100ml of acetonitrile, then 13.3g (110mmol) of 3-bromopropene was added at 55°C, React for 2.5 hours, filter, wash the filter cake three times with acetonitrile, combine the filtrate and filter cake washing with acetonitrile, concentrate in vacuo, then recrystallize from petroleum ether, and dry in vacuo to obtain N-allyl-3-(4-nitrophenyl) Pyridinium quaternary ammonium salt 31.6g, yield 98.4%.

Embodiment 3

[0030] N-allyl-3-(4-nitrophenyl)pyridine quaternary ammonium salt

[0031] 20g (100mmol) of 3-(4-nitrophenyl)pyridine and 0.65g (10mmol) of zinc powder were added to a reaction vessel containing 100ml of acetonitrile, then 14.5g (120mmol) of 3-bromopropene was added at 60°C, React for 2 hours, filter, wash the filter cake three times with acetonitrile, combine the filtrate and filter cake washing with acetonitrile, concentrate in vacuo, then recrystallize from petroleum ether, and dry in vacuo to obtain N-allyl-3-(4-nitrophenyl) Pyridinium quaternary ammonium salt 31.3g, yield 97.5%.

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Abstract

The invention discloses a method for preparing 4-(piperidine-3-yl)aniline. The method is characterized by comprising the steps that a salifying reaction is carried out, wherein 3-(4-nitrophenyl)pyridine and 3-halogenated propylene react to obtain N-allyl-3-(4-nitrophenyl)pyridine quaternary ammonium salt; a reduction reaction is carried out, wherein N-allyl-3-(4-nitrophenyl)pyridine quaternary ammonium salt is mixed with zinc chloride, and then sodium borohydride is added for reduction to obtain 4-(piperidine-3-yl)aniline. According to the method, use of precious metal is avoided, production cost of the intermediate 4-(piperidine-3-yl)aniline is greatly lowered, conditions are mild, nitryl and a pyridine ring are subjected to reduction at a time, a good yield is obtained, and the method is especially suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of an anticancer drug niraprabab intermediate 4-(piperidin-3-yl)aniline. Background technique [0002] Niraparib is an oral poly ADP-ribose polymerase (PARP) inhibitor that inhibits cellular repair of DNA damage. The inhibitor is currently in the third phase of clinical trials. The latest results show that Niraparib has a particularly good therapeutic effect on a variety of cancers, such as ovarian cancer, breast cancer, and prostate cancer. [0003] As a PARP inhibitor, it will inhibit the activity of cellular PARP. For cancer cells with BRCA gene mutations, if PARP activity is further inhibited, these cells will generate a lot of DNA damage when they divide, leading to the death of cancer cells. However, normal cells can still repair DNA without PARP because of the presence of BRCA, but the effect is worse, but they can survive. The test re...

Claims

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Application Information

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IPC IPC(8): C07D211/26
CPCC07D211/26
Inventor 王传秀
Owner QINGDAO YUNTIAN BIOTECH
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