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Method for preparing N-coffee acyl tryptamine by one-step process

A technology of acyltryptamine and coffee, applied in the field of drug synthesis, can solve the problems of being unsuitable for large-scale industrial production and long reaction steps, and achieve the effects of facilitating large-scale industrial production, mild reaction conditions, and reducing costs

Active Publication Date: 2013-09-18
盱眙凌凯医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above synthesis method, the two phenolic hydroxyl groups of caffeic acid are first protected. Although the generation of by-products is reduced, the synthesis method has long reaction steps and needs to be purified by column chromatography, which is not suitable for large-scale industrial production.

Method used

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  • Method for preparing N-coffee acyl tryptamine by one-step process
  • Method for preparing N-coffee acyl tryptamine by one-step process
  • Method for preparing N-coffee acyl tryptamine by one-step process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]Add 10g of caffeic acid and 8.89g of tryptamine into a three-necked reaction flask and dissolve in 100mL of N,N-dimethylformamide, and dissolve all of the caffeic acid and tryptamine under stirring to form a reaction solution. Add 15g of 1-hydroxybenzotriazole and 21.1g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride into the reaction solution, after the addition, cool the reaction solution to 0°C, and then 14.3gN,N-diisopropylethylamine was added dropwise to the reaction solution. After the addition, the temperature of the reaction solution was raised to 30° C. for 10 hours until the reaction was complete. Concentrate the reaction solution to remove N,N-dimethylformamide, add 200mL of ethyl acetate and 100mL of 1mol / L hydrochloric acid aqueous solution to the residue, stir for 0.5 hours, let stand to separate layers, separate the upper organic phase and wash with 100mL of saturated carbonic acid Wash once with sodium hydrogen aqueous solution, dry with a...

Embodiment 2

[0035] Add 18g of caffeic acid and 16g of tryptamine into a three-neck reaction flask and dissolve in 200mL of N,N-dimethylacetamide, and dissolve all of the caffeic acid and tryptamine under stirring to form a reaction solution. Add 67.2g of diisopropylcarbodiimide and 23g of N-hydroxysuccinimide into the reaction solution, after the addition, cool the reaction solution to -2°C, then add 20.2g of triethylamine dropwise into the reaction solution . After the addition, the temperature of the reaction solution was raised to 25° C. for 8 hours until the reaction was complete. Concentrate the reaction solution to remove N,N-dimethylacetamide, add 400mL of isopropyl acetate and 200mL of 1mol / L sulfuric acid aqueous solution to the residue, stir for 0.8 hours and then separate the layers, separate the upper organic phase and use 200mL saturated Wash once with aqueous sodium bicarbonate solution, dry with anhydrous sodium sulfate, filter to obtain the filtrate, and concentrate the f...

Embodiment 3

[0037] Add 7.2g of caffeic acid and 6.4g of tryptamine into a three-necked reaction flask and dissolve in 80mL of N-methylpyrrolidone, and stir to dissolve all of the caffeic acid and tryptamine to form a reaction solution. Add 16.5g of dicyclohexylcarbodiimide and 10.9g of 1-hydroxy-7-azobenzotriazole to the reaction solution, after the addition, cool the reaction solution to 2°C, then add 6.3g of pyridine dropwise to the reaction solution in the liquid. After the addition, the temperature of the reaction solution was raised to 35° C. for 12 hours until the reaction was complete. Concentrate the reaction solution to remove N-methylpyrrolidone, add 150mL of dichloromethane and 80mL of 1mol / L formic acid aqueous solution to the residue, stir for 0.5 hours, let stand to separate layers, separate the upper organic phase and wash with 80mL of saturated sodium bicarbonate aqueous solution Once, dry with anhydrous sodium sulfate, filter to obtain the filtrate, concentrate the filtr...

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Abstract

The invention provides a method for preparing a caffeic acid derivative N-coffee acyl tryptamine by a one-step process, which belongs to the technical field of pharmaceutical synthesis and is used for solving the problems that the N-coffee acyl tryptamine prepared in the prior art is low in yield, the reaction steps are tedious and the existing method is not suitable for large-scale industrial production and the like. The preparation method comprises the following steps of: carrying out condensation reaction for 8 hours-12hours on caffeic acid and tryptamine until the reaction is complete at the temperature of 25 DEG C-35 DEG C in solvent under the condition of a condensation agent, a condensation activating agent and organic alkaline; removing the solvent from the condensation reaction liquid; adding extracting agent and an acid aqueous solution into the leftover; layering to obtain an organic phase; washing, drying and filtering the organic phase to obtain filtrate; and concentrating the filtrate to obtain the N-coffee acyl tryptamine. The used materials of the N-coffee acyl tryptamine prepared by the one-step process are cheap and easily available, green and environment-friendly, short in synthesis route, simple in reaction condition, simple in post-treatment and convenient for large-scale industrial production. Moreover, the obtained N-coffee acyl tryptamine is high in yield and high in purity.

Description

technical field [0001] The invention relates to a method for preparing caffeic acid derivatives, in particular to a method for preparing caffeic acid derivative N-caffeoyltryptamine in one step, and belongs to the technical field of drug synthesis. Background technique [0002] Caffeic acid derivatives are natural antioxidants, and their antioxidant activities are mainly reflected in many aspects such as scavenging free radicals, chelating metal ions, inhibiting the formation of lipid catalase and the oxidation of low-density lipoproteins. Utilizing their antioxidant properties can prevent many diseases, such as cancer, diabetes, cardiovascular disease, Alzheimer's disease and Parkinson's disease, etc. [0003] N-caffeoyltryptamine is a kind of caffeic acid derivatives, CAS registration number is: 945453-47-4, its chemical name is (E)-N-(2-(1H-indol-3-yl)ethyl) -3-(3,4-dihydroxyphenyl)acrylamide, its structural formula is: [0004] [0005] In the prior art, there are t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/16
Inventor 李志强王伸勇王晓俊胡隽恺
Owner 盱眙凌凯医药科技有限公司
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