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

A cyclopropane amide and diallyl technology is applied in the fields of medicine and pharmaceutical preparation, can solve the problems of inability of cyclopropane amide hydrochloride and industrialized production, and achieves the advantages of improved safety, improved yield and avoided product loss. Effect

Active Publication Date: 2015-01-07
暨明医药科技(苏州)有限公司
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Problems solved by technology

[0008] 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

[0037] 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 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, washed with 10 liters of hydrochloric acid and 10 liters of water, dried over anhydrous sodium sulfate for 0.5 hour, filtered to remove the solid, and the filtrate was reduced to Concentrate under reduced pressure to remove the solvent, and finally retain the volume of the mixed solution after rotary evaporation to be 27 liters to obtain the ring-opened product N,N-diallyl-(1R, 2R)-2-hydroxymethyl in the form of black oil containing dichloromethane Base-1-(2-thiophene)cyclopropane (Formula 5) solution, this mixture was directly put into the next reaction without further purification. LC-MS character...

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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

technical field [0001] The invention belongs to the field of medicine, in particular to the field of medicine preparation, and more specifically relates to a specific serotonin and norepinephrine reuptake inhibitor N,N-diallyl-(1R, 2R The preparation method of )-2-aminomethyl-1-(2-thiophene)cyclopropaneamide hydrochloride. Background technique [0002] Depression is a common mental illness. With the increase of social pressure, experts predict that depression will become the second largest disease in the world in 20 years. Depression is associated with an imbalance of various neurotransmitters in the brain, such as norepinephrine (NE), dopamine, and serotonin (5-HT). Tricyclic antidepressants (TCAs) are currently commonly used clinical antidepressants, but because they have no selectivity for NE and 5-HT, the side effects of the drugs are obvious. [0003] Milnacipran (Milnacipran), developed by the Pierre Fabre company in France, is a specific 5-hydroxytryptamine (5-HT) a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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