Preparation method of hordenine hydrochloride

Abstract

The invention discloses a preparation method of hordenine hydrochloride. The preparation method comprises the following steps: taking 4-(2-bromoethyl)phenol as a raw material, adding ethanol to prepare a solution, dropwise adding excessive dimethylamine solution, and stirring at a lower temperature to carry out amination reaction to obtain hordenine hydrobromide. The proper excessive dimethylamine is adopted, so that the quaternization side reaction is effectively inhibited, the solvent dispersion effect is also played, the contact reaction opportunity of the hordenine product generated in the first reaction and the 4-(2-bromoethyl)phenol added later is greatly reduced, the high product yield can be kept, and meanwhile the low preparation cost is achieved; 4-(2-bromoethyl) phenol is added into ethanol to prepare a dilute solution of ethanol, and the dilute solution of ethanol is dropwise added into a dimethylamine solution to improve the dispersity of 4-(2-bromoethyl) phenol in a reaction system and inhibit quaternization side reaction; and the amination reaction is carried out by stirring at a relatively low temperature of 10-25 DEG C, so that the occurrence of quaternization side reaction is inhibited, and a relatively good reaction effect is achieved.

Description

technical field [0001] The invention relates to the technical field of hordenine synthesis and preparation, in particular to a preparation method of hordenine hydrochloride. Background technique [0002] Hordenine [also known as hordenine; hordenine; Anhaline; Eremursine; Peyocactine; International Chemical Federation name: 4-[2-(dimethylamino)ethyl]phenol; 4-(2-Dimethylaminoethyl)phenol (structural formula IV ); CAS: 539-15-1; Molecular formula: C10H15NO; Molecular weight: 165.24; white orthorhombic prism crystals (ethanol or benzene-petroleum ether), needle crystals (water), melting point 117~118°C, boiling point 173°C (11mmHg ), sublimation at 140-150°C. Very soluble in ethanol, chloroform and ether, 7g soluble in 1000ml water, slightly soluble in benzene, toluene and xylene, almost insoluble in petroleum ether. It can act on adrenaline receptors, relax bronchial smooth muscle, constrict blood vessels, pressurize blood vessels, raise blood pressure and excite the centra...

AI Technical Summary

Problems solved by technology

[0015] ②β-Phenylethylamine Derivatives.1 Tertiary and Quaternary Salts; p-alkoxybenzaldehyde as raw material, prepared by condensation, hydroxylamination, decarboxymethylation, and dealkylation; the route is long, the cost is high, and there is no industrial application value

[0017] ③A New Synthesis of Hordenine and Other p-Dialkylaminoethylphenols and Some of Their Derivatives (new synthesis method of hordenine and other p-dialkylaminoethylphenols and their derivatives); raw materials are not easy to obtain, and the yield is low

The disadvantage of this route is that the preparation process of 2-bromo1-(4-methoxyphenyl)ethane is more complicated, and the sealing operation needs to use a pressure reactor, which increases the equipment cost; BBr3 is more irritating and the operation difficulty increases , many wastes, high production cost

[0022] ⑤Under the action of methanol and sodium triacetoxy borohydride, it is obtained by reacting p-hydroxyphenylethylamine and paraformaldehyde. This route has short steps and good conversion rate, but it is prone to polymerization reaction, and triacetoxy borohydride The price of sodium is expensive, the price of raw materials is high, there are many three wastes, and the cost is high

[0026] ⑦Using methyl p-hydroxyphenylacetate and dimethylamine as raw materials, hordenine hydrochloride was prepared through amination and reduction, with a total yield of about 65%; however, a large amount of sodium borohydride and trifluorotrifluoride were used, which were relatively expensive. Using boron tetrahydrofuran as a reducing agent and catalyst, more by-products and wastes are produced at the same time, and the cost of three wastes is high, resulting in high production costs

[0034] At present, the above preparation methods all have no industrialized production value

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