Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of 2-aminoindane derivative and product of 2-aminoindane derivative

A synthesis method and aminoindan technology are applied in the preparation of aminohydroxy compounds, the preparation of amino compounds from amines, the preparation of carbon-based compounds, etc., and can solve the problems of difficult operation, harsh reaction conditions, and complicated reaction steps, and achieve easy operation, The effect of mild reaction conditions and simple reaction steps

Active Publication Date: 2016-08-24
LONGXINING SHANGHAI PHARMA TECH CO LTD
View PDF7 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these prior art methods often have defects such as harsh reaction conditions, cumbersome reaction steps, and difficult operation.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 2-aminoindane derivative and product of 2-aminoindane derivative
  • Synthesis method of 2-aminoindane derivative and product of 2-aminoindane derivative
  • Synthesis method of 2-aminoindane derivative and product of 2-aminoindane derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] And, described synthetic method comprises the following steps:

[0040] (1) Using compound A1 as a starting material, carry out a bromination reaction to obtain intermediate A2;

[0041] (2) The intermediate A2 is prepared by the Gabriel reaction to obtain the intermediate A3;

[0042] (3) adding hydrazine hydrate to the intermediate A3, performing a hydrolysis reaction to generate hydrazone simultaneously, and obtaining the intermediate A4;

[0043] (4) The intermediate A4 is subjected to a hydrolysis reaction to obtain the target product 2-aminoindane derivative A;

[0044] Among them, R 1 and R 2 Each independently selected from: H, C1-C30 alkanyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C3-C30 cycloalkenyl, C2-C30 alkynyl, C1- C30 alkoxy group, C7-C30 aromatic hydrocarbon group, C6-C30 aromatic hydrocarbon group, C4-C30 heterocyclic aromatic hydrocarbon group.

[0045] In a preferred embodiment, the synthesis method comprises the following steps:

[0046] (1) Disso...

Embodiment 1

[0063] The synthesis of embodiment 1 compound 1

[0064]

[0065] (1) Synthesis of intermediate 12

[0066] Dissolve 96.1g of compound 11 (0.5mol) in 500ml of ethyl acetate at room temperature, and slowly add bromine 80g (0.5mol) dropwise below 10°C. React until complete, add dropwise 1000ml of water, quench the layering, wash the organic phase once with 1000ml saturated brine, dry over anhydrous sodium sulfate and concentrate to dryness to obtain 135.5g (yield 98%) of yellow oily liquid, which is the intermediate Body 12.

[0067] (2) Synthesis of intermediate 13

[0068] At room temperature, 135.5g of intermediate 12 (0.5mol) and 101.87g of phthalimide potassium salt (0.55mol) were added to 1355ml of DMF, and stirred overnight (about 20 hours) at room temperature, the reaction solution It was dark brown, and TLC monitored the reaction until it was complete. After the reaction was complete, the reaction solution was poured into 6775ml of water, and a large amount of sol...

Embodiment 2

[0074] The synthesis of embodiment 2 compound 2

[0075]

[0076] (1) Synthesis of intermediate 22

[0077] Dissolve 81.1g of compound 21 (0.5mol) in 500ml of ethyl acetate at room temperature, keep below 10°C, slowly add 80g (0.5mol) of bromine dropwise, keep stirring at 20°C for 30 minutes, monitor by TLC After the reaction is complete, 1000ml of water is added dropwise to quench the layering, the organic phase is washed once with 1000ml of saturated brine, dried over anhydrous sodium sulfate and concentrated to dryness to obtain 120.54g of yellow oily liquid (99% yield), which is the intermediate Body 22.

[0078] (2) Synthesis of intermediate 23

[0079] At room temperature, 120.54g of intermediate 22 (0.5mol) and 101.87g of phthalimide potassium salt (0.55mol) were added to 1355ml of DMF, and stirred and reacted at room temperature for 2 hours. Brown, TLC monitors the reaction until complete, after the reaction is complete, the reaction solution is poured into 6775m...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a synthesis method of a 2-aminoindane derivative. According to the method, 5,6disubstituted 1-indanone is used as a staring raw material; bromination reaction is firstly performed; then, Gabriel reaction is performed; next, hydrazine hydrate is added; hydrolysis reaction is performed, and meanwhile, hydrazone is generated; finally, strong alkali is added into a high-boiling-point solvent to perform heating hydrolysis; the target product of the 2-aminoindane derivative is prepared. The invention also provides the 2-aminoindane derivative prepared by the synthesis method. Compared with the synthesis method of the 2-aminoindane derivative in the prior art, the synthesis method provided by the invention has the advantages that the reaction raw materials are cheap; the reaction condition is mild; the reaction steps are simple; the operation is easy; the yield of the obtained product is higher; the synthesis method is suitable for industrial production. Therefore good application prospects and market potentials are realized.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a pharmaceutical intermediate, in particular to a synthesis method of a 2-aminoindane derivative and a 2-aminoindane derivative product obtained by the synthesis method. Background technique [0002] 2-aminoindan and its derivatives are common and widely used pharmaceutical intermediates, for example, 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride can be used It is used in the synthesis of β2 adrenoceptor agonists for indications such as asthma and chronic obstructive pulmonary disease; as another example, the antihypertensive drug delapril and the antiarrhythmic drug ambroxidine are used in their respective preparation processes. to 2-aminoindan; in addition, EP1018514A1 discloses an indane derivative used as an NF-KB inhibitor, etc. [0003] Also provide some synthetic methods of 2-aminoindane derivatives in the prior art, as EP1018514A1 provides a ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C217/74C07C209/68C07C211/42
CPCC07C45/63C07C209/68C07C213/08C07C249/16C07D209/48C07C49/755C07C251/84C07C217/74C07C211/42C07C49/697
Inventor 朱宁李春成朱献明
Owner LONGXINING SHANGHAI PHARMA TECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com