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Synthesis method of 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride

A technology of benzylamine hydrochloride and trifluoromethyl, which is applied in the field of synthesis of 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride to achieve easy control and yield The effect of high rate and short route

Active Publication Date: 2021-01-08
阿里生物新材料(常州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis method of 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride is rarely reported in the literature

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0019] A kind of synthetic method of 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride, this synthetic method comprises the steps:

[0020] (1) According to the mass ratio of compound A, compound E, and methyl iodide as 20:10-12:15-18, the solid-liquid g / mL ratio of compound A and n-butyllithium is 1:2, n-butyllithium, The volume ratio of tetrahydrofuran is 1:7, take the material, add compound A, compound E, and tetrahydrofuran into the reactor, stir evenly, protect with nitrogen, cool to -80~-75°C, add n-butyllithium, and keep warm for 1~2h , add methyl iodide, raise the temperature to 30-35°C, and stir for 15-20h to obtain compound B;

[0021] (2) According to the mass ratio of compound B, tert-butyl carbamate, tridibenzylideneacetone dipalladium, 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene, and potassium carbonate is: 8~9:3~5:0.5~1:0.5~1:6~10, the solid-liquid g / mL ratio of compound B and dioxane is 1:15, and the material is taken, and compound B, amino ...

Embodiment 1

[0024] A kind of synthetic method of 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride, this synthetic method comprises the steps:

[0025] (1) Add 20g of compound A, 10g of compound E, and 280mL of tetrahydrofuran into the reactor, stir well, protect with nitrogen, cool to -80°C, add 40mL of n-butyllithium, keep warm for 1h, add 15g of methyl iodide, and heat up to 30°C, Stir for 15 hours, HPLC detection, the reaction of the raw materials is complete, under the ice-water bath, add saturated ammonium chloride (120mL) dropwise, extract with ethyl acetate (250mL*2), concentrate the organic phase, and after the concentration is complete, 16.9g of yellow oil is obtained, and the compound B, the yield is 79.89%, and the purity is 96.3%;

[0026] (2) 8g compound B, 3g tert-butyl carbamate, 0.5g tridibenzylideneacetone dipalladium, 0.4g 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene, Put 6g of potassium carbonate and 120mL of dioxane into the reactor, nitrogen replace...

Embodiment 2

[0030] A kind of synthetic method of 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride, this synthetic method comprises the steps:

[0031] (1) Add 20g of compound A, 11g of compound E, and 280mL of tetrahydrofuran into the reactor, stir evenly, protect with nitrogen, cool to -78°C, add 40mL of n-butyllithium, keep warm for 1.5h, add 17g of methyl iodide, and heat up to 33°C , stirred for 18 hours, detected by HPLC, the reaction of the raw materials was completed, under the ice-water bath, saturated ammonium chloride (120mL) was added dropwise, extracted with ethyl acetate (250mL*2), the organic phase was concentrated, and after the concentration was completed, 17.5g of yellow oil was obtained. Compound B, the yield was 82.73%, and the purity was 95.8%;

[0032] (2) 8g of compound B, 4g of tert-butyl carbamate, 0.8g of tridibenzylideneacetone dipalladium, 0.7g of 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene, Put 8g of potassium carbonate and 120mL of dioxane ...

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Abstract

The invention belongs to the technical field of medical intermediates, and particularly relates to a synthesis method of 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride. A compound A and a compound E are used as initial raw materials for the first time to form a compound B, then the compound B is subjected to a reaction to form a compound C, and the compound C is used for preparingthe 2-fluoro-3-methyl-4-(trifluoromethyl) benzylamine hydrochloride.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical intermediates, and specifically relates to a synthesis method of 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride. Background technique [0002] The compound 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, there are few reports on the synthesis of 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] Technical problem to be solved by the present invention: Aiming at the problems mentioned above, a method for synthesizing 2-fluoro-3-methyl-4-(trifluoromethyl)benzylamine hydrochloride is provided. [0004] In order...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/26C07C25/13C07C269/06C07C271/28C07C209/62C07C211/52
CPCC07C17/26C07C269/06C07C209/62C07C25/13C07C271/28C07C211/52
Inventor 许义波戴红升
Owner 阿里生物新材料(常州)有限公司
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