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Preparation method of 2,3-dichlorophenylpiperazine hydrochloride

A technology of dichlorophenylpiperazine and hydrochloride, applied in 2 fields, can solve the problems of high raw material cost of aripiprazole, complicated operation steps and the like, and achieve the effects of high product yield and simple operation

Pending Publication Date: 2018-07-20
苏州宝圣医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The present invention provides a preparation method of 2,3-dichlorophenylpiperazine hydrochloride in order to solve the problems of high raw material cost and cumbersome operation steps in the preparation method of aripiprazole in the prior art

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  • Preparation method of 2,3-dichlorophenylpiperazine hydrochloride
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  • Preparation method of 2,3-dichlorophenylpiperazine hydrochloride

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preparation example Construction

[0025] In a typical embodiment of this application, a method for preparing 2,3-dichlorophenylpiperazine hydrochloride is proposed, and the method includes:

[0026] (A) Cyclization reaction of bis(2-chloroethyl)amine hydrochloride and 2,3-dichloroaniline in N,N-dimethylformamide single solvent to obtain 2,3-dichlorophenyl Piperazine hydrochloride step.

[0027] In another typical embodiment of the present application, a method for preparing 2,3-dichlorophenylpiperazine hydrochloride is proposed, and the method includes:

[0028] (A1) Diethanolamine is used as raw material to generate bis(2-chloroethyl)amine hydrochloride through chlorination reaction;

[0029] (A2) Cyclization reaction of bis(2-chloroethyl)amine hydrochloride and 2,3-dichloroaniline in N,N-dimethylformamide single solvent to obtain 2,3-dichlorophenyl Piperazine hydrochloride step.

[0030] In the technical scheme of the present invention, a single N,N-dimethylformamide solvent is used, so that the 2,3-dichlorophenylpi...

Embodiment 1

[0032] (1) Preparation of bis(2-chloroethyl)amine hydrochloride

[0033]

[0034] Weigh 200g of diethanolamine and add 800ml of toluene into a 2L three-necked flask, stir to dissolve, keep the temperature at 20-30°C, add 566g of thionyl chloride dropwise, heat up to 50°C, keep it for 3h and evaporate the solvent under reduced pressure to recover toluene.

[0035] Add 100ml of toluene to the remaining residue, stir at 20-30°C for 30min, filter, and dry to obtain 322g of bis(2-chloroethyl)amine hydrochloride as a white solid, yield: 94.7%.

[0036] (2) Preparation of 2,3-dichlorophenylpiperazine hydrochloride

[0037]

[0038] Weigh 130g of 2,3-dichloroaniline into a 500ml three-necked flask, add 144g of bis(2-chloroethyl)amine hydrochloride, then add 200ml of DMF (N,N-dimethylformamide), and stir for 5min. , Heated to 140-145°C, reacted for 6 hours, HPLC monitored the reaction to complete, and then cooled to 5-10°C to obtain 200 g of light yellow solid. The above solid is dissolved in...

Embodiment 2

[0042] (1) Preparation of bis(2-chloroethyl)amine hydrochloride

[0043] Dissolve 523 g (4.4 mol) of thionyl chloride in 100 mL of chloroform, place it in a four-necked flask equipped with a reflux condenser and an ice-water bath, stir, and absorb the tail gas with water. Slowly add a mixture of 215 g (2 mol) of diethanolamine and 150 mL of chloroform. During the addition, control the temperature of the reaction solution to not exceed 30°C, and the addition time is about 3 h. After the addition is complete, remove the ice-water bath and react at room temperature for 1 h, then slowly increase the temperature. After the solid is completely dissolved, the temperature is increased to 50°C, and the reaction is continued for 0.5 h. Stop heating, cool to room temperature, and filter with suction to obtain a slightly white and yellowish green solid , Recrystallized with absolute ethanol to obtain 291g of white needle-like crystals, with a yield of 81%, and a melting point of 214~216°C. ...

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Abstract

The invention relates to a preparation method of 2,3-dichlorophenylpiperazine hydrochloride. The method comprises the steps as follows: step 1, diethanol amine is used as a raw material and subjectedto a chlorination reaction to produce bis(2-chloroethyl)amine hydrochloride; step 2, bis(2-chloroethyl)amine hydrochloride and 2,3-dichloroaniline are subjected to a cyclization reaction in an N,N-dimethylformamide single solvent at 130-155 DEG C, and 2,3-dichlorophenylpiperazine hydrochloride is obtained. The product prepared with the preparation method has higher yield and has the purity up to 98% and is obtained with the technology in one step, and the operation is simple.

Description

Technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 2,3-dichlorophenylpiperazine hydrochloride. Background technique [0002] Aripiprazole is used to treat various types of schizophrenia. Foreign clinical trials have shown that this product has obvious effects on both positive and negative symptoms of schizophrenia, and can also improve the accompanying emotional symptoms and reduce the recurrence rate of schizophrenia. [0003] Aripiprazole is the first stabilizer of the dopamine system. It has a significant effect on both positive and negative symptoms of schizophrenia. The US Food and Drug Administration approved it for marketing on November 15, 2002. It has a significant effect on the DA nerve system. Two-way regulation, it is a stabilizer of DA transmitter. It has high affinity with D2, D3, 5-HT1A and 5-HT2A receptors. It produces anti-schizophrenia effects by partially agonizing D2 ...

Claims

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Application Information

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IPC IPC(8): C07D295/073
CPCC07D295/073
Inventor 魏海洋胡立文王征
Owner 苏州宝圣医药科技有限公司
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