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Preparation method of N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride

A cyclopropane amide and diallyl technology, which is applied in the field of medicine and pharmaceutical preparation, can solve the problems of industrialized production and the inability of cyclopropane amide hydrochloride, and achieve the advantages of improving yield, improving safety and avoiding product loss. Effect

Active Publication Date: 2013-08-14
暨明医药科技(苏州)有限公司
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Problems solved by technology

[0011] The present invention aims at the problem that N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thiophene)cyclopropaneamide hydrochloride cannot be industrially produced in the pharmaceutical field, and provides a A preparation method of N,N-diallyl-(1R, 2R)-2-aminomethyl-1-(2-thiophene) cyclopropaneamide hydrochloride, the preparation method is based on cyclopropane lactone Based on intermediates, N,N-diallyl-(1R, 2R)-2-aminomethyl-1-(2-thiophene ) the method of cyclopropaneamide hydrochloride, its concrete reaction formula is as follows:

Method used

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  • Preparation method of N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride

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Embodiment 1

[0041] Dissolve 1.82 kg of 1-(2-thiophene) cyclopropane lactone (Formula 2) and 2.67 kg of anhydrous aluminum trichloride in 20 liters of dichloromethane, cool the reaction system to -10°C, and add 3.89 kg of diene dropwise Propylamine. After the reaction system was stirred for 30 minutes, 11 liters of hydrochloric acid was added to the reaction system, and the organic layer was separated, and then washed with 10 liters of hydrochloric acid and 10 liters of water respectively, dried with anhydrous sodium sulfate for 0.5 hours, filtered to remove solids, and the filtrate was reduced. Concentrate under pressure to remove the solvent. Finally, the volume of the mixed liquid after rotary evaporation is 27 liters, and a black oily N,N-diallyl-(1R, 2R)-2-hydroxymethyl containing dichloromethane is obtained. 1-(2-thiophene)cyclopropane (formula 5) solution, this mixed solution is directly put into the next reaction without further purification. LC-MS characterization of purity> 99%, ...

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Abstract

The invention belongs to the medicine field, especially belongs to the medicine preparation field, and concretely relates to a preparation method of a preparation method of a specific 5-hydroxytryptamine and noradrenaline reuptake inhibitor N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride. The preparation method of N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride is provided against a problem that N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride cannot be industrially produced in the pharmaceutical field at present. The preparation method is characterized in that N,N-diallyl-(1R,2R)-2-aminomethyl-1-(2-thienyl)cyclopropanecarboxamide hydrochloride is obtained through a series of reactions comprising ring opening, sulfonation, azidation, reduction and salting of a cyclopropane lactone intermediate which is treated as a base.

Description

[0001] Technical field [0002] The present invention belongs to the field of medicine, in particular to the field of preparation of medicines, and more specifically to a specific serotonin and norepinephrine reuptake inhibitor N,N-diallyl-(1R, 2R) ) Preparation method of 2-aminomethyl-1-(2-thiophene) cyclopropane amide hydrochloride. [0003] Background technique [0004] Depression is a common mental illness. With the increase of social pressure, experts predict that depression will become the second most common disease in the world in 20 years. Depression is related to the imbalance of various neurotransmitters in the brain, such as norepinephrine (NE), dopamine, and serotonin (5-HT). At present, tricyclic antidepressants (TCA) are commonly used clinically, but because they are not selective for NE and 5-HT, the side effects of drugs are obvious. [0005] Milnacipran, developed by the French company Pierre Fabre, is a specific serotonin (5-HT) and norepinephrine (NE) reuptake in...

Claims

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Application Information

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IPC IPC(8): C07D333/24
Inventor 陈剑戈李斌峰
Owner 暨明医药科技(苏州)有限公司
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