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Preparation method of 4-(3-piperidino) aniline and tartrate thereof

A technology of tartrate and methyl nitrophenylacetate, applied in directions such as organic chemistry, can solve the problems of expensive reagents and high equipment requirements, and achieve the effects of low price, low cost and reduction of reaction costs

Inactive Publication Date: 2017-06-23
CHINA PHARM UNIV
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Problems solved by technology

The advantage of this method is that its route is shorter, but shortcoming is also very obvious: starting material 3-pyridine boronic acid, and catalyzer [1,1 '-bis(diphenylphosphino) ferrocene]palladium dichloride and Reagents such as platinum oxide are expensive, and the reaction requires high-pressure hydrogenation, which requires high equipment

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  • Preparation method of 4-(3-piperidino) aniline and tartrate thereof
  • Preparation method of 4-(3-piperidino) aniline and tartrate thereof
  • Preparation method of 4-(3-piperidino) aniline and tartrate thereof

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Embodiment Construction

[0030] The present invention will be further described below through the examples, but the examples do not limit the protection scope of the present invention.

[0031] 1. Preparation of methyl p-nitrophenylacetate (3)

[0032] Dissolve 20g (0.11mol) of p-nitrobenzoic acid in 300ml of methanol, add 2ml of concentrated sulfuric acid, heat up to reflux after addition, and react for 2 hours. Distill off part of the solvent under reduced pressure, add saturated aqueous sodium bicarbonate solution to the residue to adjust the pH to 7-8, add 200ml of water, extract with ethyl acetate (100ml×3), combine the organic phases, and wash with saturated brine (100ml×2) , dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 21.2 g of light yellow needle-like crystals. The crude product was used directly in the next step without purification.

[0033] 2. Preparation of methyl 4-cyano-2-(4-nitrophenyl)butyrate (4)

[0034] The crude product from the previou...

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a preparation method of 4-(3-piperidino) aniline and tartrate thereof. The preparation method is characterized by comprising the following steps: taking p-nitrophenylacetic acid as a raw material, carrying out four-step reaction of esterification, Michael addition, reductive cyclization and lactam reduction to obtain 4-(3-piperidino) aniline free amine, and carrying out reaction on the free amine and tartaric acid to obtain the tartrate of the 4-(3-piperidino) aniline. The preparation method has the advantages of simpleness, convenience and availability in raw materials, low cost, mild reaction condition, simpleness in operation and the like. A chemical formula is shown in the description.

Description

[0001] Technical field: [0002] The invention belongs to the field of organic synthetic chemistry, in particular to a method for preparing 4-(3-piperidinyl)aniline and tartrate thereof [0003] technical background: [0004] Niraparib (Niraparib, chemical name is 2-[4-((3S)-3-piperidinyl) phenyl]-2H-indazole-7-carboxamide) is an oral drug developed by Tesaro Company in the United States. Poly ADP-ribose polymerase (PARP) targeted inhibitors are mainly used clinically for cancers with BRCA1 / 2 gene mutations, such as ovarian cancer and breast cancer. At present, it has passed the Phase III clinical trial for advanced ovarian cancer, and its clinical data It can extend the median progression-free survival of patients by 280% to 22 months. Therefore, the drug has great application prospects in the field of treatment of ovarian cancer. The literature (Organic Process Research & Development, 2011, 15 (4): 831-840) reported the first kilogram-level synthetic method of niraparib, wh...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/26
CPCC07D211/26
Inventor 薛晓文班浩罗国虎贺宇辰李嘉宾
Owner CHINA PHARM UNIV
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