Preparation method of N,N-dimethyl-5-hydroxytryptamine

Abstract

The invention provides a preparation method of N,N-dimethyl-5-hydroxytryptamine, which comprises the following steps: preparing 5-hydroxytryptamine hydrochloride as an initial raw material, and reacting with formaldehyde and sodium cyanoborohydride under the action of Friedel-Crafts catalysts (zinc trifluoroacetate and zinc chloride) to obtain the N,N-dimethyl-5-hydroxytryptamine. The method has the advantages of simple synthesis process, mild synthesis conditions, high yield of 90% or more, good quality and content of 99.5% or more. The method for synthesizing the N,N-dimethyl-5-methoxytryptamine, provided by the invention, is easy for industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a preparation method of N,N-dimethyl-5-hydroxytryptamine. Background technique [0002] N,N-dimethyl-5-hydroxytryptamine, also known as bufotryptamine, is a light yellow solid that was first found in toads and later in other invertebrates and some plants; its structure is similar to that of N, N-Dimethyltryptamine is similar to 5-methoxy-N,N-dimethyltryptamine; binds to 5-HT2A receptors in vitro and binds to 4-bromo-2,5-dimethoxyphenyl Isopropylamine (DOB) has a similar affinity. It can be used both as a psychotomimetic and as a biomarker in the diagnosis of various psychiatric disorders such as schizophrenia and autism. [0003] The synthesis process of N,N-dimethyl-5-hydroxytryptamine is mainly as follows. The first synthesis process uses 5-hydroxyindole as the starting material, and undergoes three-step reactions of oxalylation, aminatio...

AI Technical Summary

Problems solved by technology

[0003] The synthesis process of N,N-dimethyl-5-hydroxytryptamine is mainly as follows. The first synthesis process uses 5-hydroxyindole as the starting material, and undergoes three-step reactions of oxalylation, amination and reduction to obtain the product N,N-Dimethyl-5-hydroxytryptamine; this process uses the reducing agent lithium aluminum hydride, which has strict requirements on reaction conditions and post-processing operations, and is not suitable for process scale-up, only suitable for laboratory synthesis

The second synthesis process (Fischer synthesis process) is to use 4-methoxyphenylhydrazine hydrochloride as the starting material, and carry out ring-closure reaction with N,N-dimethylaminobutyraldehyde diethyl acetal under acid catalyst to obtain N , N-dimethyl-5-hydroxytryptamine, the yield is 70%; although the process route of this method is short, the raw materials 4-methoxyphenylhydrazine hydrochloride and N,N-dimethylaminobutyraldehyde diacetal Ethanol is expensive and difficult to obtain, resulting in high production costs, so the synthesis process is not an economical process

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