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Method for preparing R-3-methyl-1-aminoindane

A technology for aminoindane and R-3-, which is applied in the field of preparing R-3-methyl-1-aminoindane, and achieves the effects of mild process conditions, easy separation and recycling, and efficient preparation method

Inactive Publication Date: 2015-11-18
吴玲
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing 3-methyl-1-aminoindane related reports, there are few reports on how to prepare optically pure R-3-methyl-1-aminoindane

Method used

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  • Method for preparing R-3-methyl-1-aminoindane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] (1) Preparation of 3-methyl-1-indanone oxime

[0009] In a 1000ml round bottom flask, add 600ml methanol, 146g (1.0mol) 3-methyl-1-indanone, 70g (1.0mol) hydroxylamine hydrochloride, 98.4g (1.2mol) sodium acetate, reflux for 2 hours, spot plate detection 3-Methyl-1-indanone disappeared. After cooling, 4000ml of water was added to the system under stirring, and a large amount of white solid was precipitated, filtered and dried to obtain 154g of 3-methyl-1-indanone oxime, with a yield of 95.7%.

[0010] (2) Preparation of 3-methyl-1-aminoindane

[0011] In a 2000ml autoclave, add 1200ml methanol, 154g 3-methyl-1-indanone oxime, 15g Raney nickel, 200ml ammonia water, after sealing the autoclave and replacing the air, inject hydrogen to the pressure of 1.0MPa, and react at 65°C for 5h , 3-methyl-1-indanone oxime was transformed into 3-methyl-1-aminoindan, filtered and concentrated to obtain 3-methyl-1-aminoindan.

[0012] (3) Resolution of 3-methyl-1-aminoindane

[0013...

Embodiment 2

[0019] (1) Preparation of 3-methyl-1-indanone oxime

[0020] In a 1000ml round bottom flask, add 500ml methanol, 146g (1.0mol) 3-methyl-1-indanone, 83.8g (1.2mol) hydroxylamine hydrochloride, 123g (1.5mol) sodium acetate, reflux reaction for 3h, spot plate detection 3-Methyl-1-indanone disappeared. After cooling, 4000ml of water was added to the system under stirring, and a large amount of white solid was precipitated, which was filtered and dried to obtain 156g of 3-methyl-1-indanone oxime, with a yield of 96.9%.

[0021] (2) Preparation of 3-methyl-1-aminoindane

[0022] In a 2000ml autoclave, add 1000ml methanol, 156g 3-methyl-1-indanone oxime, 20g Raney nickel, 150ml ammonia water, after sealing the autoclave and replacing the air, inject hydrogen to a pressure of 1.5MPa, and react at 60°C for 7h , 3-methyl-1-indanone oxime was transformed into 3-methyl-1-aminoindan, filtered and concentrated to obtain 3-methyl-1-aminoindan.

[0023] (3) Resolution of 3-methyl-1-aminoin...

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Abstract

The invention discloses a method for preparing R-3-methyl-1-aminoindane by taking 3-methyl-1-indanone as the raw material. The method particularly comprises the steps that the 3-methyl-1-indanone is taken as the raw material, and the R-3-methyl-1-aminoindane is obtained through the operations of oxime forming, hydrogenation reduction and the like; L-mandelic acid is taken as a resolving agent to be reacted with the R-3-methyl-1-aminoindane in a solution, and diastereomeric salt of the R-3-methyl-1-aminoindane and the resolving agent is obtained, after recrystallization is conducted on the salt, alkalization is conducted, and the R-3-methyl-1-aminoindane is obtianed; solutions with the resolving agent are combined together, and after acidification is conducted, the resolving agent L-mandelic acid can be recycled. According to the method for preparing the R-3-methyl-1-aminoindane, the operation is easy, the separation efficiency is high, the resolving solutions and the resolving solvents are easy to recycle and reuse, the environmental pollution is little, and the method for preparing the R-3-methyl-1-aminoindane is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of an optically pure chiral compound, in particular to a method for preparing R-3-methyl-1-aminoindan by using 3-methyl-1-indanone as a raw material. Background technique [0002] R-3-methyl-1-aminoindan is a very important class of chiral pharmaceutical intermediates. Among the existing reports on 3-methyl-1-aminoindan, there are few reports on how to prepare optically pure R-3-methyl-1-aminoindan. How to obtain an efficient and convenient method for preparing R-3-methyl-1-aminoindan is the problem to be solved by the present invention. Contents of the invention [0003] The purpose of the present invention is to provide a low-cost and simple method for obtaining optically pure R-3-methyl-1-aminoindan by resolution. The present invention is a kind of use 3-methyl-1-indanone as raw material to prepare R-3-methyl-1-aminoindan, the concrete operation is as follows: take 3-methyl-1-indanone as raw material...

Claims

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Application Information

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IPC IPC(8): C07C211/42C07C209/26C07C209/88
Inventor 吴玲
Owner 吴玲