Preparation method of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethylamine

A dimethylamino and furanyl technology is applied in the field of preparation of 2-[[[5-methyl-2-furyl]methyl]thio]ethylamine, and achieves simple process, high yield and high purity Effect

Active Publication Date: 2017-07-28
HEBEI HAILI FRAGRANCES CO LTD
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Although the yield and purity have improved compared t

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preparation example Construction

[0023] The present invention provides a kind of preparation method of 2-[[[5-(dimethylamino)methyl-2-furyl]methyl]thio]ethylamine, comprising the following steps:

[0024] (1) Mix dimethylamine hydrochloride alcohol solution, paraformaldehyde and quaternary ammonium salt, heat up to 50-70°C, add furfuryl alcohol to the reaction system, keep the temperature constant, and carry out the first condensation reaction. After the reaction is completed , remove the solvent to obtain the intermediate;

[0025] (2) Mix the intermediate with cysteamine hydrochloride, concentrated hydrochloric acid and perchloric acid, and carry out the second condensation reaction at 15-25°C to obtain a compound containing 2-[[[5-(dimethylamino)methanol Base-2-furyl] methyl] thio] ethylamine hydrochloride mixed solution;

[0026] (3) Alkalinizing the mixed solution, then extracting with dichloromethane, and distilling the resulting extract to obtain 2-[[[5-(dimethylamino)methyl-2-furyl]methyl] Thio]ethy...

Embodiment 1

[0064] (1) dimethylamine hydrochloride 85.6kg, methyl alcohol 30kg, drop into 500L reactor, obtain dimethylamine hydrochloride alcoholic solution; Be that 40wt.% dimethylamine aqueous solution is dimethylamine hydrochloride alcoholic solution with concentration Adjust the pH value to 5.5; mix the dimethylamine hydrochloride alcohol solution after adjusting the pH value with 31.5kg of paraformaldehyde and 0.1kg of tetrabutylammonium bromide, and heat up to 60°C under stirring conditions, Add 98 kg of furfuryl alcohol dropwise to the system, and keep the temperature of the system at 60°C; after the dropwise addition, keep the temperature constant, and carry out the first condensation reaction; Distill under reduced pressure to distill out methanol and water. After the system temperature reaches 60°C, keep 60°C and continue to distill for 20 minutes. No more liquid is distilled out, and the intermediate is obtained at room temperature;

[0065] (2) Add 117kg of cysteamine hydroch...

Embodiment 2

[0071] (1) 91kg of dimethylamine hydrochloride and 49kg of methanol are put into a 500L reactor to obtain dimethylamine hydrochloride alcoholic solution; it is 40wt.% dimethylamine aqueous solution to make the dimethylamine hydrochloride alcoholic solution Adjust the pH value to 6.5; mix the dimethylamine hydrochloride alcohol solution after adjusting the pH value with 33kg of paraformaldehyde and 0.5kg of tetrabutylammonium bromide, heat up to 65°C under stirring conditions, and pour into the system Add 100kg of furfuryl alcohol dropwise, and keep the temperature of the system at 65°C; after the dropwise addition, keep the temperature constant, and carry out the first condensation reaction; after reacting for 4 hours, lower the temperature to 35°C, and then reduce the pressure to 0.09kPa to carry out the decompression Distillation, methanol and water are distilled out. After the system temperature reaches 60°C, keep 60°C and continue to distill for 15 minutes. No more liquid i...

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Abstract

The invention provides a preparation method of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethylamine. The preparation method comprises mixing a dimethylamine hydrochloride solution, polyformaldehyde and a quaternary ammonium salt, heating the mixture to 50 to 70 DEG C, adding furfuryl alcohol into the reaction system, carrying out a first condensation reaction process to obtain an intermediate, mixing the intermediate, cysteamine hydrochloride, concentrated hydrochloric acid and perchloric acid, carrying out a second condensation reaction process at the system temperature of 15 to 25 DEG C to obtain a mixed solution of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethylamine hydrochloride, alkalifying the mixed solution, extracting the solution through dichloromethane and distilling the extract to obtain 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethylamine. The preparation method has the advantages of high yield, high product purity, simple processes and industrialization easiness.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a preparation method of 2-[[[5-(dimethylamino)methyl-2-furyl]methyl]thio]ethylamine. Background technique [0002] 2-[[[5-(Dimethylamino)methyl-2-furyl]methyl]thio]ethylamine, also known as aminoethyl sulfide, is a pharmaceutical intermediate, mainly used for the synthesis of gastric medicine hydrochloric acid The intermediate of ranitidine. The traditional production process of aminoethyl sulfide is a two-stage method, that is, firstly synthesize dimethylamine hydrochloride with hydrochloric acid and dimethylamine as raw materials, mix dimethylamine hydrochloride with formaldehyde aqueous solution and furfuryl alcohol, and perform the first condensation Reaction, after the reaction is completed, add sodium hydroxide to neutralize, and after liquid separation, the upper layer oil phase will be distilled to obtain 2-[[[5-(dimethylamino)methyl-2-furyl]methyl]t...

Claims

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Application Information

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IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 李文革张云堂张玉芬邵帅赵卫时红粉
Owner HEBEI HAILI FRAGRANCES CO LTD
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