A kind of process improvement method of preparing 2-aminobutyronitrile

A kind of aminobutane cyanide and pressure control technology, applied in the preparation of carboxylic acid nitrile, the preparation of carboxylic acid amide, chemical instruments and methods, etc., can solve the problem of low yield, improve yield, make full use of, and simplify separation and purification operations Effect

Inactive Publication Date: 2011-12-28
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD +1
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  • Application Information

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Problems solved by technology

[0005] The disadvantage of this patent is that, using n-propionaldehyde and sodium cyanide as starting materials, 2-aminobutyramide racemate is obtained through strecker reaction and hydrolysis, and the two-step yield is only 40%, which is too low.

Method used

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  • A kind of process improvement method of preparing 2-aminobutyronitrile

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Experimental program
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Embodiment 1

[0024] In the reactor of 1000mL, add successively the sodium cyanide aqueous solution that is made into by the water of 73.5g (1.5mol) sodium cyanide, 171g, 60.2g (1.125mol) ammonium chloride; Pass into ammonia gas under stirring, ice-water bath cooling, The temperature of the reaction system was maintained within 10°C, and ammonia gas was passed for 2 hours; after passing through, 0.5g of benzyltriethylammonium chloride was added, and while the reaction temperature was maintained, 43.5g (0.75mol) of n-propionaldehyde, 1.5 The dropwise addition was completed within 1 hour; after continuing to stir for 30 minutes, feed ammonia gas to make the pressure 0.3 MPa, rise to room temperature (20-25° C.) and react for 20 hours. After the reaction was completed, extract with dichloromethane (100mL×3), combine the organic phases, wash the organic phase once with saturated brine, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure to obtain 49g of a yell...

Embodiment 2

[0026] The water phase after extraction and separation of Example 1 was placed in a 1000mL reaction kettle, and 40.1g (0.75mol) of ammonium chloride and 36.8g (0.75mol) of solid sodium cyanide were added successively, ammonia gas was introduced under stirring, and cooled in an ice-water bath , the temperature of the reaction system was maintained within 10°C, and the ammonia gas was passed for 2 hours; after the pass was completed, and the reaction temperature was maintained, 43.5g (0.75mol) of n-propionaldehyde was slowly added dropwise, and the dropwise addition was completed within 1.5 hours; after continuing to stir for 30 minutes Feed ammonia gas to make the pressure 0.3 MPa, rise to room temperature (20-25° C.) and react for 20 hours. After the reaction was completed, extract with dichloromethane (100mL×3), combine the organic phases, wash the organic phase once with saturated brine, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure t...

Embodiment 3

[0028] The water phase after extraction and separation of Example 2 was placed in a 1000mL reaction kettle, 40.1g (0.75mol) of ammonium chloride and 36.8g (0.75mol) of solid sodium cyanide were added in sequence, ammonia gas was introduced under stirring, and cooled in an ice-water bath , the temperature of the reaction system was maintained within 10°C, and the ammonia gas was passed for 2 hours; after the pass was completed, and the reaction temperature was maintained, 43.5g (0.75mol) of n-propionaldehyde was slowly added dropwise, and the dropwise addition was completed within 1.5 hours; after continuing to stir for 30 minutes Feed ammonia gas to make the pressure 0.3 MPa, rise to room temperature (20-25° C.) and react for 20 hours. After the reaction is complete, extract with dichloromethane (100mL×3), combine the organic phases, wash the organic phase once with saturated brine, dry over anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure to o...

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Abstract

This article relates to a process improvement method for the preparation of levetiracetam intermediate 2-aminobutyridine from antiepileptic drugs. The method of the invention improves the traditional Strecker reaction, and remarkably improves the reaction efficiency through the airtight ammonia pressure condition and the use of excess cyanide.

Description

technical field [0001] The invention relates to a chiral drug intermediate, specifically a method for synthesizing the important intermediate 2-aminobutyridine of the antiepileptic drug levetiracetam. Background technique [0002] Epilepsy is a chronic recurrent short-term brain dysfunction syndrome caused by a variety of etiologies. The long-term recurrent seizures of the disease seriously affect the patient's quality of life and social work ability, and cause great harm to individuals and society. Levetiracetam (Keplan, Levetiracetam, chemical name: (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide) is a new type of antiepileptic drug developed by UCB Company in Belgium. Compared with similar drugs, levetiracetam has high therapeutic index, high safety index, can be used for single treatment, does not interact with other antiepileptic drugs, has mild side effects, good tolerance, and various pharmacokinetic indexes It is the only antiepileptic drug reported so far that has the uni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/24C07C253/00C07D207/27C07C237/06C07C231/06
Inventor 王立新许景刚徐小英张从金明俊男陈一王文
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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