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A kind of synthetic method of Mitazenol

A synthetic method, the technology of mirazol, applied in the direction of organic chemistry, etc., can solve the problems of hindering the ring-closing reaction, many impurities in the reaction, and difficult ring-closing, etc., so as to ensure the yield and stability, the safety of the process route, and the reaction product high rate effect

Active Publication Date: 2017-06-20
SHANXI KANGBAO BIOLOGICAL PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the 2-{N"-[N'-(2-chloroethyl)-N'-methyl-β-phenethylamine-α-yl]-amino}-3-hydroxymethyl group cannot be removed in time If the hydrogen chloride on the pyridine hydrochloride is then difficult to continue the ring closure, and the hydrogen chloride generated by the ring closure reaction can react with 2-amino-3-hydroxymethylpyridine to generate hydrochloride, which hinders the ring closure reaction. Therefore, The above reaction has many impurities and extremely low yield

Method used

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  • A kind of synthetic method of Mitazenol
  • A kind of synthetic method of Mitazenol
  • A kind of synthetic method of Mitazenol

Examples

Experimental program
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Effect test

Embodiment 1

[0040]Add 3g of ethyl 2-aminonicotinate (0.0181mol) and 50mL of tetrahydrofuran into the three-necked flask, add 5.4g of sodium borohydride (0.1426mol) powder under stirring, continue stirring at 60°C for 15min, add dropwise 30mL of methanol, and reflux React until TLC (chloroform:methanol=4:1) monitors the completion of the reaction, concentrate in vacuum while hot, distill 40mL of the mixed solution, add 1gNaOH, hydrolyze at 70-80°C for 7-8h, separate the organic phase, anhydrous sulfuric acid Sodium-dried and concentrated to obtain 1.6 g of light yellow solid powder of 2-amino-3-pyridinemethanol (Intermediate A), m.p.67.5-68°C, yield 70%.

[0041]

[0042] Get 7.3g N-(2-chloroethyl)-N-methyl-α-chloro-β-phenethylamine (0.0314mol) and join in the mixed solution of 7mL chloroform and 3mL water, 3g Intermediate A (0.0242 mol) was dissolved in 18mL chloroform with 0.075mL ethanol, slowly added dropwise to the above mixed solution, reacted for 5-6h, and solid K was added to th...

Embodiment 2

[0048] Add 5g of ethyl 2-aminonicotinate (0.0302mol) and 80mL of tetrahydrofuran into the three-neck flask, add 13g of sodium borohydride (0.2416mol) powder under stirring, continue stirring at 65°C for 15min, add dropwise 65mL of methanol, and react under reflux To TLC (chloroform: methanol = 4: 1) to monitor the completion of the reaction, concentrated in vacuum while hot, distilled 40mL of the mixed solution, added 1gNaOH, hydrolyzed at 70 ~ 80 ° C for 7 ~ 8h, separated the organic phase, anhydrous sodium sulfate Drying and concentration gave 2.7 g of 2-amino-3-pyridinemethanol (Intermediate A) light yellow solid powder, m.p.67.5-68°C, yield 75%.

[0049] Get 10g of N-(2-chloroethyl)-N-methyl-α-chloro-β-phenylethylamine (0.0430mol) into a mixed solution of 15mL of dichloromethane and 4mL of water, 4g of Intermediate A ( 0.0323mol) was dissolved in 25mL dichloromethane with 0.1mL ethanol, slowly added dropwise to the above mixed solution, reacted for 5-6h, and solid K was ad...

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Abstract

The invention discloses a 1-(3-hydroxymethylpyridine-2-yl)-4-methyl-2-phenylpiperazine synthesis method. The method includes: dissolving N-(2-chloroethyl)-N-methyl-alpha-chlorine-beta phenethylamine in mixed solution of water and a nonpolar solvent to obtain solution A, and dissolving 2-amino-3-hydroxymethylpyridine into a nonpolar solvent containing a small quantity of low carbon alcohols to obtain solution B; dripping the solution B into the solution A to obtain an intermediate by reaction, dissolving the intermediate into an anhydrous high-boiling-point polar solvent, and dripping into an anhydrous high-boiling-point polar solvent of inorganic iodides under inert gas shielding to realize reaction for obtaining 1-(3-hydroxymethylpyridine-2-yl)-4-methyl-2-phenylpiperazine. By two steps for synthesis of 1-(3-hydroxymethylpyridine-2-yl)-4-methyl-2-phenylpiperazine, oxidization of the intermediate due to direct high-temperature reaction can be avoided by specific solvent systems, and reaction stability and yield are improved.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and relates to a method for synthesizing mirtazapine intermediate mirtazapine. Background technique [0002] Mirtazapine, chemical name 1,2,3,4,10,14b hexahydro-2-methylpyrazinyl[2,1-a]pyrido[2,3-c]azepine, molecular formula C 17 h 19 N 3 , with a molecular weight of 265.36, is an antidepressant and an antagonist of central presynaptic membrane α2 receptors, which can enhance adrenergic nerve conduction and block central 5-HT2 and 5-HT3 receptors. The two enantiomers of mirtazapine have antidepressant activity, the L-isomer blocks α2 and 5-HT2 receptors, and the D-isomer blocks 5-HT3 receptors. The antihistamine receptor (H1) properties of mirtazapine act as a sedative. The drug is well tolerated, has almost no anticholinergic effect, and has no effect on the cardiovascular system. Mirtazapine is the world's first antidepressant drug with dual inhibitory eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14
CPCC07D471/14
Inventor 周满祥申云飞周楷王帆刘宇鹏
Owner SHANXI KANGBAO BIOLOGICAL PROD
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