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Preparation method of substituted benzoxazole derivative

A technology of oxazole and nucleophilic substitution, applied in the field of new preparation of pharmaceutical intermediates, can solve problems such as difficult synthesis

Inactive Publication Date: 2018-03-09
湖南华腾制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methanamine is difficult at present

Method used

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  • Preparation method of substituted benzoxazole derivative
  • Preparation method of substituted benzoxazole derivative
  • Preparation method of substituted benzoxazole derivative

Examples

Experimental program
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Embodiment 1

[0023] (1) Synthesis of 5-methoxybenzo[d]oxazole-2-thiolate potassium

[0024] Add 40g of 2-amino-4-methoxyphenol to 380ml of pyridine, add 63g of potassium ethylxanthate, heat under reflux and stir for 5 hours, concentrate to remove most of the pyridine, add dilute hydrochloric acid and ethyl acetate, divide The organic phase was collected, dried and concentrated, and the residue was separated on a column to obtain 51 g of potassium 5-methoxybenzo[d]oxazole-2-thiolate.

[0025] (2) Synthesis of 5-methoxy-2-chlorobenzo[d]oxazole

[0026] Add 50g of 5-methoxybenzo[d]oxazole-2-thiolate potassium to 1000ml of chloroform, cool to 0°C, pour in chlorine to saturation, keep at 0°C and stir for 2 small tests, then warm to room temperature to continue Stir for 5 hours, concentrate, add water and ethyl acetate, extract and separate, collect the organic phase, separate, dry, concentrate, and separate the residue on a silica gel column to obtain 36g of 5-methoxy-2-chlorobenzo[d ] Oxazole.

[00...

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Abstract

The invention discloses a preparation method of a substituted benzoxazole derivative, i.e., (1-(5-methoxybenzo[d]oxazole-2-yl)piperidin-4-yl)methylamine. According to the preparation method, 2-amino-4-methoxyphenol is taken as a starting raw material, and a target product is obtained by carrying out ring closing, chlorination, nucleophilic substitution, ammonolysis and reduction. The compound is an important medical intermediate.

Description

Technical field [0001] The invention relates to a novel preparation method of pharmaceutical intermediates, in particular to a preparation method of (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methylamine A method of preparation. technical background [0002] The compound (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methylamine, the structural formula is: [0003] [0004] This compound (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methylamine and related derivatives have a wide range of applications in medicinal chemistry and organic synthesis. At present, the synthesis of (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methylamine is difficult. Therefore, it is necessary to develop a synthetic method that is easy to obtain, easy to operate, easy to control the reaction, and suitable for the overall yield. Summary of the invention [0005] The present invention discloses a method for preparing (1-(5-methoxybenzo[d]oxazol-2-yl)piperidin-4-yl)methylamine, with 2-amino-4-m...

Claims

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Application Information

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IPC IPC(8): C07D413/04
CPCC07D413/04
Inventor 不公告发明人
Owner 湖南华腾制药有限公司
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