Preparation method of 2-aminobutanamide hydrochloride

A technology of aminobutyronitrile hydrochloride and aminobutyramide, which is applied in the field of preparation of 2-aminobutyramide hydrochloride, can solve the problems of increased by-products, less main products, troublesome post-processing, etc., and achieves high yield, Fewer by-products and mild reaction conditions

Inactive Publication Date: 2010-08-25
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this synthesis method is: when preparing 2-aminobutyronitrile, the reaction temperature is 60 ℃, such a high reaction temperature increases the by-products of the reaction, troublesome post-processing, resulting in a decline in yield; in the process of alcoholysis Reaction temperature is room temperature, and temperature is too low, mainly generates 2-aminobutyrimidic acid ethyl ester hydrochloride at lower temperature; And main product is few, and productive rate is lower

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Preparation of 2-aminobutyronitrile amine hydrochloride:

[0017] Add 35.4g of ammonium chloride, 46mL of ammonia water (30%), 110.2g of 28% sodium cyanide aqueous solution and 160mL of water into a 1000mL three-necked bottle at 10-15°C, stir magnetically, start to add 45mL of n-propionaldehyde dropwise, 1.5 The addition was completed after 1 hour, the reaction was detected by TLC, the color was developed in an iodine cylinder, and the reaction was completed after 8 hours of heat preservation. Extract with 1,2-dichloroethane (50mL×3), combine the organic phases, fully dry with excess anhydrous sodium sulfate, then pass hydrogen chloride gas at room temperature until pH = 4, filter with suction, rinse with acetone, and get off-white 65.5 g of solid 2-aminobutyronitrile hydrochloride (the filtrate was directly recycled), yield 80.5%, m.p 144-146°C.

[0018] (2) Preparation of 2-aminobutanamide hydrochloride:

[0019] Add 200mL of isopropanol and 30g of 2-aminobutyro...

Embodiment 2

[0022] (1) Preparation of 2-aminobutyronitrile amine hydrochloride:

[0023] Add 39.8g of ammonium chloride, 49mL of ammonia water (30%), 111.5g of 28% sodium cyanide aqueous solution and 160mL of water into a 1000mL three-necked bottle at 5-10°C, stir magnetically, and start to add 45mL of n-propionaldehyde dropwise, 1.5 The addition was completed after 1 hour, the reaction was detected by TLC, the color was developed in an iodine cylinder, and the reaction was completed after 8 hours of heat preservation. Extract with 1,2-dichloroethane (60mL×3), combine the organic phases, fully dry with excess anhydrous sodium sulfate, and then pass hydrogen chloride gas at room temperature until pH = 3, filter with suction, rinse with acetone, and get off-white 45.1 g of solid 2-aminobutyronitrile hydrochloride (the filtrate was directly recycled), yield 55.4%, m.p 143-146°C.

[0024] (2) Preparation of 2-aminobutanamide hydrochloride:

[0025] Add 155mL of isopropanol and 22g of 2-amin...

Embodiment 3

[0028] (1) Preparation of 2-aminobutyronitrile amine hydrochloride:

[0029] Add 33.2g of ammonium chloride, 49mL of ammonia water (30%), 121.6g of 28% sodium cyanide aqueous solution and 160mL of water into a 1000mL three-necked flask at 0-5°C, stir magnetically, and start to add 45mL of n-propionaldehyde dropwise, 1.5 The addition was completed after 1 hour, the reaction was detected by TLC, the color was developed in an iodine cylinder, and the reaction was completed after 8 hours of heat preservation. Extract with 1,2-dichloroethane (55mL×3), combine the organic phases, fully dry with excess anhydrous sodium sulfate, then pass hydrogen chloride gas at room temperature until pH = 4, filter with suction, and rinse with acetone to obtain off-white 50.2 g of solid 2-aminobutyronitrile hydrochloride (the filtrate was directly recycled), yield 61.7%, m.p 144-146°C.

[0030] (2) Preparation of 2-aminobutanamide hydrochloride:

[0031] Add 245mL of isopropanol and 35g of 2-amino...

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Abstract

The invention discloses a preparation method of 2-aminobutanamide hydrochloride, which comprises the following steps that: ammonium chloride, ammonia (30 percent) and sodium cyanide are added into aqueous solvent, and propyl aldehyde is dripped in at 5 to 10DEG C to react for 4 to 10h and to be extracted; organic phase is combined and dried; hydrogen chloride gas is fed in at room temperature until the pH value is 3 to 4, filtered to prepare 2-amino nitrile hydrochloride; and the product is dissolved in isopropanol, the temperature goes up, the hydrogen chloride gas is fed in until the solution is saturated, reaction is carried out for 4 to 5h, the product is cooled to room temperature and filtered, thereby a target product is obtained. The preparation method of 2-aminobutanamide hydrochloride has the advantages of mild reaction conditions, high yield, few by-products and the like.

Description

technical field [0001] The invention relates to the synthesis of chemical substances, in particular to a preparation method of 2-aminobutanamide hydrochloride. Background technique [0002] 2-Aminobutyramide is an important compound among amide derivatives, widely used in the preparation of medicine and pesticide, and is an important organic synthesis intermediate. Synthesis of (S)-alpha-ethyl-2-oxo-1-acetamide pyrrolidine (levetiracetam) as it was applied to the antiepileptic drug. [0003] The existing method for synthesizing 2-aminobutanamide hydrochloride (Journal of the American Chemical Society (1960), 82 696-8, Journal of Organic Chemistry (1962), 27, 798-802) is: n-propionaldehyde and sulfurous acid Sodium hydrogen and sodium cyanide are reacted to prepare 2-aminobutyronitrile, and then hydrogen chloride is passed through at room temperature to hydrolyze the 2-aminobutyronitrile, and 2-aminobutyronitrile hydrochloride is prepared by alkoxylation. The advantage of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/06C07C231/06
Inventor 洪镛裕白春梅刘艳刘现林赵志伟
Owner EAST CHINA NORMAL UNIV
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