Preparation method of cis-2, 6-dimethyl piperidine

A technology of dimethylpiperidine and lutidine, which is applied in the field of piperidine compound preparation, can solve the problems of low content of cis-2,6-dimethylpiperidine and the like, so as to facilitate industrialized large-scale production and improve yield , Improve the effect of hydrogenation activity

Pending Publication Date: 2021-08-17
ANHUI XINGYU CHEM
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Problems solved by technology

[0008] Aiming at the problem of low content of cis-2,6-dimethylpiperidine obtained by the existing preparation method, the present invention provides a preparation method of cis-2,6-dimethylpiperidine, which can increase the content of cis-2,6-dimethylpiperidine Content of Dimethylpiperidine

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  • Preparation method of cis-2, 6-dimethyl piperidine
  • Preparation method of cis-2, 6-dimethyl piperidine

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The preparation method of the cis-2,6-dimethylpiperidine of the present embodiment comprises the following steps:

[0030] A. Under hydrogen protection conditions, add 100g 2,6-lutidine, 40g distilled water, 5g composite catalyst (the mass ratio of palladium carbon, nickel powder and metal iron acetate is 1:0.05:0.05) into the autoclave Carry out the reaction, the reaction pressure of carrying out the reaction is 30kg / cm 2 , the reaction temperature is 120°C, the reaction time is 5h, and after the reaction is completed, the crude product of 2,6-dimethylpiperidine is obtained by suction filtration;

[0031] B. Cool the crude 2,6-dimethylpiperidine obtained in step A to room temperature, take out the reaction mixture, and take the supernatant after standing to obtain 2,6-dimethylpiperidine.

[0032] Since the product 2,6-dimethylpiperidine and the raw material 2,6-lutidine have a low boiling point, a relatively simple and fast gas chromatography method is adopted in this...

Embodiment 2

[0053] The preparation method of the cis-2,6-dimethylpiperidine of the present embodiment comprises the following steps:

[0054] A. Under hydrogen protection conditions, add 100g 2,6-lutidine, 50g distilled water, 6g composite catalyst (the mass ratio of palladium carbon, nickel powder and metal iron acetate is 1:0.05:0.08) into the autoclave Carry out the reaction, the reaction pressure of carrying out the reaction is 40kg / cm 2 , the reaction temperature is 150°C, the reaction time is 6h, and after the reaction is completed, the crude product of 2,6-dimethylpiperidine is obtained by suction filtration;

[0055] B. Cool the crude 2,6-dimethylpiperidine obtained in step A to room temperature, take out the reaction mixture, and take the supernatant after standing to obtain 2,6-dimethylpiperidine.

[0056] The cis content of the 2,6-dimethylpiperidine mixture was detected to be 14.9% by gas chromatography (GC).

Embodiment 3

[0058] The preparation method of the cis-2,6-dimethylpiperidine of the present embodiment comprises the following steps:

[0059] A. Under hydrogen protection conditions, add 100g 2,6-lutidine, 60g distilled water, 8g composite catalyst (the mass ratio of palladium carbon, nickel powder and metal iron acetate is 1:0.1:0.05) into the autoclave Carry out the reaction, the reaction pressure of carrying out the reaction is 35kg / cm 2 , the reaction temperature is 140°C, the reaction time is 8h, after the reaction is completed, the crude product of 2,6-dimethylpiperidine is obtained by suction filtration;

[0060] B. Cool the crude 2,6-dimethylpiperidine obtained in step A to room temperature, take out the reaction mixture, and take the supernatant after standing to obtain 2,6-dimethylpiperidine.

[0061] The cis content of the 2,6-dimethylpiperidine mixture was detected to be 15.3% by gas chromatography (GC).

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Abstract

The invention discloses a preparation method of cis-2, 6-dimethyl piperidine, and belongs to the technical field of piperidine compound preparation. The method comprises the following steps: A, under a nitrogen protection condition, adding 2, 6-dimethyl pyridine, distilled water and a composite catalyst into a high-pressure reaction kettle for reaction, and after the reaction is finished, carrying out suction filtration to obtain a 2, 6-dimethyl piperidine crude product; and B, cooling the 2, 6-dimethyl piperidine crude product obtained in the step A to room temperature, taking out a reaction mixture, standing, and taking supernatant liquid to obtain the high-purity cis-2, 6-dimethyl piperidine. The content of the cis-2, 6-dimethyl piperidine is about 15%, and the cis-2, 6-dimethylpiperidine is qualified if the content is greater than 10%; the catalyst is easy to prepare, low in cost and reusable.

Description

technical field [0001] The invention belongs to the technical field of preparation of piperidine compounds, and more specifically relates to a preparation method of cis-2,6-dimethylpiperidine. Background technique [0002] cis-2,6-dimethylpiperidine is a main intermediate of the recent new coronavirus drug, the usual method to prepare 2,6-dimethylpiperidine, of which cis-2,6-dimethylpiperidine can only be made To 5-6%, most of it is the invalid trans-2,6-dimethylpiperidine. The current synthesis route of cis-2,6-dimethylpiperidine: Synthesis of cis-2,6-dimethylpiperidine through 2,6-lutidine, as follows: [0003] [0004] The catalytic hydrogenation of pyridines can be roughly divided into four methods in the treatment of catalytic methods: 1. The method of direct catalytic hydrogenation using supported nano-noble metals; 2. The method of first using the salt-forming reaction and then catalytic hydrogenation; 3. 1. The method of indirect salt formation; 4. The method of...

Claims

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Application Information

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IPC IPC(8): C07D211/02C07D211/12B01J31/04B01J23/44B01J23/755
CPCC07D211/02C07D211/12B01J31/04B01J23/44B01J23/755B01J2231/646B01J35/19
Inventor 张升张宽宇万红根张太亮刘进水
Owner ANHUI XINGYU CHEM
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