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The synthetic method of (r)-1-(4-methylphenyl) ethylamine

The technology of a methyl phenyl group and a synthesis method is applied in the synthesis field of -1-ethylamine, and can solve the problems of complicated steps, difficult purification of products, and high cost of raw materials

Active Publication Date: 2020-12-18
LIANHE CHEM TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem to be solved by the present invention is that the existing synthetic method of (R)-1-(4-methylphenyl)ethylamine has defects such as high raw material cost, complicated steps, high operation risk or difficult purification of the product.

Method used

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  • The synthetic method of (r)-1-(4-methylphenyl) ethylamine
  • The synthetic method of (r)-1-(4-methylphenyl) ethylamine
  • The synthetic method of (r)-1-(4-methylphenyl) ethylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0104]

Embodiment 1a

[0106] Add 0.89 g of acetic anhydride dropwise to 1 g of (R)-1-phenylethylamine, raise the temperature to 55°C and stir for 2 hours, then add 2.4 g of 15% sodium hydroxide aqueous solution dropwise, cool to room temperature, filter, and use the filter cake After washing once with water, vacuum drying at 65-70°C gave 1.35 g of white solid with a yield of 100% and a purity of 100% by HPLC.

Embodiment 1b

[0108] Dissolve 1 gram of (R)-1-phenylethylamine in 5 grams of toluene, then add 1.07 grams of propionic anhydride dropwise, raise the temperature to 55°C and stir for 2 hours, concentrate to remove toluene, and add 2.4 grams of 15% sodium hydroxide dropwise The aqueous solution was cooled to room temperature, filtered, the filter cake was washed once with water, and then vacuum-dried at 65-70°C to obtain 1.46 g of white solid with a yield of 100% and a purity of 100%.

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Abstract

The invention discloses a method for synthesis of (R)-1-(4-methyl phenyl) ethylamine. The method includes: subjecting a compound 3 to deacylation to obtain (R)-1-(4-methyl phenyl) ethylamine in a C4-C10 monoalcohol solvent and in the presence of alkali metal hydroxide, wherein R refers to ethanoyl, propionyl or butyryl. The method is low in synthesis cost, simple in step, safe in operation, low inby-products, simple in aftertreatment, easy to purify intermediate products and final products, high in whole yield, high in final product purity and easy in industrialization.

Description

technical field [0001] The invention relates to a synthesis method of (R)-1-(4-methylphenyl)ethylamine. Background technique [0002] (R)-1-(4-methylphenyl)ethylamine is a colorless liquid chemical at room temperature. Molecular formula is C 9 h 13 N, the molecular weight is 135.21. (R)-1-(4-Methylphenyl)ethylamine is the key intermediate of the new drug Y-39983 developed by Mitsubishi Tanabe Pharmaceuticals for the treatment of glaucoma. The new drug is currently in the second phase of clinical research. The structural formula of (R)-1-(4-methylphenyl)ethylamine is as follows: [0003] [0004] At present, the main synthetic route of (R)-1-(4-methylphenyl)ethylamine that has been reported is as follows: [0005] 1. Document Tetrahedron: Asymmetry, 4(9), 2095-100; 1993 records: [0006] [0007] This route leads to the reductive amination method of norephedrine that p-methylacetophenone is converted into (R)-1-(4-methylphenyl) ethylamine, and defect is that the n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/62C07C211/27
CPCC07C209/62C07C231/02C07C231/12C07C211/27C07C233/05C07C233/13Y02P20/55
Inventor 蔡栋材朱文忠李永锋
Owner LIANHE CHEM TECH