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Preparation method for 3-(piperidine-4-yl)-pyridazine

A kind of technology of piperidine and pyridazine, applied in the field of preparation of pyridazine derivative 3--pyridazine, can solve problems such as synthesis difficulty

Inactive Publication Date: 2015-03-11
湖南华腾制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis of 3-(piperidin-4-yl)-pyridazine is difficult at present

Method used

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  • Preparation method for 3-(piperidine-4-yl)-pyridazine
  • Preparation method for 3-(piperidine-4-yl)-pyridazine
  • Preparation method for 3-(piperidine-4-yl)-pyridazine

Examples

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Embodiment 1

[0022] (1) Synthesis of 1-benzyl-4-(pyridazin-3-yl)piperidin-4-ol

[0023] Add 16g of 3-bromopyridazine into 190ml of anhydrous tetrahydrofuran, cool down to -78°C, add 50ml of 2.5M n-butyllithium dropwise, stir for 30min, then add 22g of N-benzylpiperidone solution in tetrahydrofuran dropwise, Stir at -78°C for 2 hours, warm up to room temperature, add saturated ammonium chloride, add water and ethyl acetate for extraction and separation, collect the organic phase, dry, concentrate, and the residue is put on a silica gel column to obtain 21g 1-benzyl-4-( Pyridazin-3-yl)piperidin-4-ol.

[0024] (2) Synthesis of 3-(1-benzyl-4-yl-1,2,3,6-tetrahydro)pyridazine

[0025] Add 20g of 1-benzyl-4-(pyridazin-3-yl)piperidin-4-ol to 200ml of hydrochloric acid, heat to reflux and stir for 10 hours, add aqueous sodium hydroxide solution to adjust pH=10, add ethyl acetate to extract The liquid was separated, the organic phase was collected, dried and concentrated to obtain 15 g of 3-(1-ben...

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Abstract

The invention discloses a preparation method for 3-(piperidine-4-yl)-pyridazine. N-benzyl piperidone is adopted as the starting material, and by means of addition, elimination, reduction and debenzylation reaction, the target product can be obtained. The compound is an important pharmaceutical intermediate.

Description

technical field [0001] The invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation method of a pyridazine derivative 3-(piperidin-4-yl)-pyridazine. technical background [0002] Compound 3-(piperidin-4-yl)-pyridazine, the structural formula is: [0003] [0004] The compound 3-(piperidin-4-yl)-pyridazine and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthesis of 3-(piperidin-4-yl)-pyridazine is relatively difficult at present. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0005] The invention discloses a method for preparing pyridazine derivative 3-(piperidin-4-yl)-pyridazine, which uses N-benzylpiperidone as a starting material, and undergoes addition, elimination, reduction, and desorption The benzyl reaction obtains th...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 陈芳军李书耘
Owner 湖南华腾制药有限公司
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