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Method for synthesis of haloperidol drug intermediate 4-chlorobutyronitrile

The technology of a kind of haloperidol and synthetic method is applied in the synthetic field of haloperidol drug intermediate 4-chlorobutyronitrile, which can solve the problems of weak sedative effect, reduce intermediate links, reduce reaction temperature and reaction time, The effect of increasing the reaction yield

Inactive Publication Date: 2016-04-20
CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The antiemetic effect is also strong, but the sedative effect is weak

Method used

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  • Method for synthesis of haloperidol drug intermediate 4-chlorobutyronitrile

Examples

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example 1

[0012] Add 1.6mol of 1-chloro-4,4-dihydroxybutylamine (2) in the reaction vessel, the mass fraction is 60% 2-nitrophenol solution (3) 2.1mol, 1.5mol of aluminum oxide, the mass fraction is 30% Cyclohexane 300ml, control the stirring speed at 130rpm, raise the solution temperature to 90°C, keep reflux for 2h, lower the solution temperature to 70°C, continue the reaction for 90min, lower the solution temperature to 6°C, let stand for 70min, the solution is separated, take out The oil layer is extracted 5 times with 50% toluene in mass fraction, washed with ammonium chloride solution, washed with 70% acrylonitrile in mass fraction, washed with 65% triethylamine in mass fraction, dehydrated with anhydrous potassium carbonate, 90% in mass fraction Recrystallized in nitromethane to obtain 136.45 g of crystalline 4-chlorobutyronitrile with a yield of 82%.

example 2

[0014] Add 1.6mol of 1-chloro-4,4-dihydroxybutylamine (2) in the reaction vessel, the mass fraction is 62% 2-nitrophenol solution (3) 2.3mol, 1.5mol of aluminum oxide, the mass fraction is 32% Cyclohexane 300ml, control the stirring speed at 150rpm, raise the solution temperature to 92°C, keep reflux for 3h, lower the solution temperature to 72°C, continue the reaction for 95min, lower the solution temperature to 7°C, let stand for 80min, the solution is separated, take out The oil layer is extracted 6 times with 52% toluene in mass fraction, washed with ammonium chloride solution, washed with 72% acrylonitrile in mass fraction, washed with 67% triethylamine, dehydrated with solid sodium hydroxide, 93% in mass fraction Recrystallized in nitromethane to obtain 141.44 g of crystalline 4-chlorobutyronitrile with a yield of 85%.

example 3

[0016] Add 1.6mol of 1-chloro-4,4-dihydroxybutylamine (2) in the reaction vessel, the mass fraction is 65% 2-nitrophenol solution (3) 2.6mol, 1.5mol of aluminum oxide, the mass fraction is 35% Cyclohexane 300ml, control the stirring speed at 170rpm, raise the solution temperature to 97°C, keep reflux for 4h, lower the solution temperature to 77°C, continue the reaction for 110min, lower the solution temperature to °C, stand still for 90min, the solution is separated, take out The oil layer is extracted 7 times with 55% toluene in mass fraction, washed with ammonium chloride solution, washed with 75% acrylonitrile in mass fraction, washed with 68% triethylamine, dehydrated with anhydrous potassium carbonate, and 98% in mass fraction Recrystallized in nitromethane to obtain 153.09 g of crystalline 4-chlorobutyronitrile with a yield of 92%.

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Abstract

A method for synthesis of the haloperidol drug intermediate 4-chlorobutyronitrile comprises the steps of adding 1.6 mol of 1-chloro-4,4-dyhydroxy butyl amine, 2.1-2.6 mol of 2-nitrophenol solution, 1.5 mol of aluminum oxide and 300 ml of cyclohexane into a reaction vessel, controlling the stirring speed to be 130-170 rpm, increasing solution temperature to 90-97 DEG C, maintaining backflow for 2-4 h, reducing solution temperature to 70-77 DEG C, conducting reaction continuously for 90-110 min, reducing solution temperature to 6-9 DEG C, standing for 70-90 min, conducting solution delamination, taking an oil layer out, conducting extraction with methylbenzene for 5-7 times, conducting washing with saline solution, propionitrile and triethylamine, conducting dehydration with a dehydrating agent, and conducting recrystallization in nitromethane, so that 4-chlorobutyronitrile crystals are obtained.

Description

technical field [0001] The invention relates to a method for synthesizing haloperidol drug intermediate 4-chlorobutyronitrile. Background technique [0002] Haloperidol is mainly used for various acute and chronic schizophrenia. It is especially suitable for acute adolescent type and paranoid schizophrenia accompanied by hostility and aggressive actions. It can also be used for other types or chronic schizophrenia that are ineffective to phenothiazine treatment, anxiety neurosis, and small doses of this product. Effective, can eliminate involuntary movement, and can reduce and eliminate accompanying mental symptoms, vomiting and intractable hiccups. This product is the main representative of butyrophenone antipsychotics, its effect is similar to that of chlorpromazine, and it has strong dopamine receptor antagonistic effect. At the same dose, its dopamine receptor antagonism effect is 20 to 40 times that of chlorpromazine, so it is a powerful low-dose antipsychotic. Featu...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C253/34C07C255/10
CPCC07C253/00C07C253/34
Inventor 关艮安
Owner CHENGDU QIANYE LONGHUA PETROLEUM ENG TECH CONSULTING
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