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Method for preparing N-(2-methyl-3-nitro)-N-propyl-1-propylamin hydrochloride

A technology of propylamine hydrochloride and nitrophenyl, which can be used in the preparation of amino compounds and organic chemistry from amines, and can solve the problems of long route, long production cycle, and many processes.

Active Publication Date: 2009-11-25
JIANGSU SKYRUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Both of the above two methods require six steps of reaction, the route is long, and highly toxic cyanide is used, resulting in many processes, long production cycle and high cost of wastewater treatment

Method used

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  • Method for preparing N-(2-methyl-3-nitro)-N-propyl-1-propylamin hydrochloride

Examples

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Embodiment 1

[0030] Synthesis of 3-(2-methyl-3-nitrophenyl)-glycidic acid methyl ester

[0031] 2-Methyl-3-nitrobenzaldehyde (50g, 0.3mol) and methyl chloroformate (39.5g, 0.36mol) were dissolved in benzene (500mL), the reaction solution was cooled to -5 degrees, and then kept below 0 degrees A methanol solution of sodium methoxide (19 g, 0.36 mol) was added dropwise. After the dropwise addition, tetrabutylammonium bromide (5 g, 0.015 mol) was added, and the mixture was kept at zero and stirred for 2 hours, and stirred overnight at room temperature. Water (200 mL) was added to the reaction solution, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate and concentrated to obtain a yellow oil (42.4 g, yield 59%).

Embodiment 2

[0033] Synthesis of 2-methyl-3-nitrophenylacetaldehyde

[0034] 3-(2-Methyl-3-nitrophenyl)-glycidic acid methyl ester (30g, 0.13mol) was dissolved in 100mL of methanol, cooled to zero in an ice bath, NaOH (5.7g, 0.14mol) was added dropwise aqueous solution (100 mL), the reaction solution was slowly raised to room temperature, and stirred for 5 hours. Concentrate and distill off methanol, control the water layer below 10°C, adjust the pH to weak acidity with concentrated hydrochloric acid, add toluene (300mL), heat to reflux for 4 hours, separate the organic layer, wash with water, dry over anhydrous sodium sulfate, and concentrate to obtain a yellow oil , standing and cooling to obtain a yellow solid (15.2 g, yield 67%).

Embodiment 3

[0036] Synthesis of N-(2-methyl-3-nitro)-N-propyl-1-propanamine hydrochloride

[0037] 2-Methyl 3-nitrophenylacetaldehyde was dissolved in methanol (10g, 0.056mol), anhydrous magnesium sulfate (10g, 0.084mol) and di-n-propylamine (8.5g, 0.084mol) were added, and then cyano Sodium borohydride (3.5g, 0.056mol) in methanol (100mL) solution, the reaction solution was stirred overnight at room temperature, filtered, the filtrate was concentrated to dryness, the residue was dissolved in dichloromethane, washed with water, the aqueous layer was extracted twice with dichloromethane, The organic phases were combined and concentrated to give a light yellow oil, which was dissolved in toluene, and the toluene solution of HCL was slowly added dropwise to precipitate a white solid, which was cooled and filtered, and the obtained solid was recrystallized with 95% ethanol to obtain the product (11.6 g, yield 79%).

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Abstract

The invention relates to a novel method for synthesizing N-(2-methyl-3-nitro)-N-propyl-1-propylamin hydrochloride only by three-step reactions, which comprises the steps of: taking 2-methyl-3-nitrobenzoic acid as a raw material, preparing epoxy propionic ether through Darzons condensation, then hydrolyzing and decarboxylating the epoxy propionic ether to obtain 2-methyl-3-nitrophenylacetaldehyde,and finally obtaining the N-(2-methyl-3-nitro)-N-propyl-1-propylamin hydrochloride by reducing ammoniation and salification. Compared with the prior method, the method has the advantages that: the method has a short route, thereby reducing working procedures and reducing production period; and the method avoids the use of virulent cyanidums, reduces the production cost for materials and three wastes and the like.

Description

technical field [0001] The invention relates to a preparation method of N-(2-methyl-3-nitro)-N-propyl-1-propanamine hydrochloride. N-(2-methyl-3-nitro)-N-propyl-1-propanamine hydrochloride is used to prepare ropinirole hydrochloride (Ropinirole hydrochloride), that is, 4-[2-(di-n-propylamine) -Ethyl]-1,3-dihydroindolin-2-one hydrochloride is a very important intermediate. Background technique [0002] Ropinirole hydrochloride is an early Parkinson's treatment drug developed by the British Smith Kline-Beecham Company. It was first listed in the UK in 1996. The trade name is It is a potent and selective non-ergot alkaloid dopamine D2-receptor agonist, which can directly stimulate striatal dopamine receptors, thereby improving slowness of movement, stiffness, tremor and depression, and improving patients' daily life ability; It can also reduce the complications caused by long-term use of levodopa. Its structural formula is as follows: [0003] [0004] N-(2-methyl 3-nit...

Claims

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Application Information

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IPC IPC(8): C07C211/29C07C209/68
Inventor 燕立波王丽王伸勇黄迎春
Owner JIANGSU SKYRUN PHARMA CO LTD
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