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The synthetic method of n-benzyl-4-methyl-3-piperidone

A synthetic method, the technology of methylpiperidine, which is applied in the field of synthesis of organic compound N-benzyl-4-methyl-3-piperidone, can solve the problems of reduced yield, complex and harsh oxidation reaction operation process, etc.

Inactive Publication Date: 2011-12-28
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The problem that this method exists is that the yield is low, only about 45%, and methyllithium is applied in this step reaction, and the requirements of the reaction operation process are relatively harsh, and there is certain danger
[0019] In the first step of the process, borane is applied to the first step of the reaction, and the requirements for the reaction operation process are relatively strict, and if it is not handled properly during the post-treatment, it will lead to an increase in by-products and reduce the yield; Relatively cumbersome, and the total yield from raw material synthesis of N-benzyl-4-methyl-1,2,3,6-tetrahydropyridine to synthesis of N-benzyl-4-methyl-3-piperidone Relatively low, generally less than 30%

Method used

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Embodiment 1

[0044] Embodiment 1, a kind of synthetic method of N-benzyl-4-methyl-3-piperidone, with 3-hydroxyl-4-picoline and benzyl chloride as starting raw materials, the following steps are carried out successively:

[0045] 1) Synthesis of the benzyl chloride salt (compound 1) of 3-hydroxyl-4-picoline

[0046] Add 6.0g (0.055mol) of 3-hydroxy-4-methylpyridine to 80ml of acetonitrile, and dropwise add an acetonitrile solution of benzyl chloride (8.5g (0.067mol) of benzyl chloride dissolved in 10ml of acetonitrile) at room temperature, and the addition is complete Finally, continue to stir at room temperature for 15 minutes, then heat up to reflux, during the heating process, the reaction system gradually becomes a homogeneous system, and the reflux reaction is overnight, and the reaction process is detected by TLC (ethyl acetate / methanol=10: 1); the reaction is complete After cooling to room temperature, 4 / 5 of the acetonitrile was distilled off under reduced pressure, and 100ml of eth...

Embodiment 2

[0061] Embodiment 2, a kind of synthetic method of N-benzyl 4-methyl-3-piperidone,

[0062] In step 1): the molar ratio of benzyl chloride and 3-hydroxyl-4-picoline is adjusted to 1.05: 1 (the addition of benzyl chloride is 7.4g (0.058mol)), and other operations are the same as in Example 1 to obtain the first The yield of the one-step target product compound 1 is 90.84%, and the purity is 95.36%.

[0063] Step 2) and step 3) are the same as in Example 1; the total yield is 86.1%.

Embodiment 3

[0064] Embodiment 3, a kind of synthetic method of N-benzyl-4-methyl-3-piperidone,

[0065] In step 1):

[0066] The reaction solvent I was tetrahydrofuran (replacing the acetonitrile in Example 1), and the other operations were the same as in Example 1. The yield of the target product Compound 1 in the first step was 88.42%, and the purity was 94.55%.

[0067] Step 2) and step 3) are the same as in Example 1; the total yield is 83.8%.

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Abstract

The invention discloses a synthesis method of N-benzyl-4-methyl-3-piperidone, using 3-hydroxy-4-methylpyridine and benzyl chloride as starting materials, comprising the following steps: 1) mixing 3-Hydroxy-4-picoline is added to the reaction solvent I, and the mixture of benzyl chloride and reaction solvent I is added dropwise at room temperature, and the temperature is raised to reflux; 2) Add the 3-hydroxyl obtained in step 1) to the alkaline aqueous solution -benzyl chloride salt and reducing agent of 4-picoline, then warming up to reflux; 3) adding the N-benzyl-3-hydroxyl-4-methylpiperidine obtained in step 2) into the reaction solvent II, dropwise Add CrO 3 solution and concentrated sulfuric acid, and react at room temperature to obtain N-benzyl-4-methyl-3-piperidone. The synthesis method has the characteristics of high total yield and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic compound N-benzyl-4-methyl-3-piperidone. Background technique [0002] N-benzyl-4-methyl-3-piperidone is an important chemical raw material, widely used in the pharmaceutical industry, and is an important intermediate for the synthesis of a new protein tyrosine kinase JAK3 inhibitor CP-690550, whose structural formula is 1: [0003] [0004] Formula 1 [0005] The synthesis of N-benzyl-4-methyl-3-piperidone reported in the literature is mainly to synthesize its intermediate product N-benzyl-4-methyl-1,2,3,6-tetrahydropyridine (its The structure is shown in formula 2), followed by hydroboration and oxidation (Tetrahedron 1970, 26, 5519-5527) to obtain N-benzyl-4-methyl-3-piperidone. [0006] [0007] Formula 2 [0008] About the preparation of N-benzyl-4-methyl-1,2,3,6-tetrahydropyridine mainly reports three kinds of methods: [0009] Document J.Am.Chem.Soc.1985,107,1768-1769 reported...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/74
Inventor 郝宝玉陈新志王帅张维汉
Owner ZHEJIANG UNIV
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