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A new method for synthesizing 2-(1-methylimidazol-5-yl)ethylamine hydrochloride
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A technology for ethylamine hydrochloride and methylimidazole, which is applied in the field of synthesizing 2-ethylamine hydrochloride, can solve the problems of long steps, low total yield, poor atom economy and the like, and achieves low production cost and reaction yield. High, easy-to-use effects
Active Publication Date: 2022-03-15
苏州莱克施德药业有限公司
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[0008] In this method, the N-3 position of imidazole and the amino group of aliphatic amine are protected by trimethylphenyl and phthaloyl, which are large steric protection groups, and then deprotected after the reaction is completed. The steps are long and the overall yield is low. , and the atomic economy is poor, resulting in a large amount of solid waste and wastewater
[0009] Other bibliographical methods also can't prepare pure 2-(1-methylimidazol-5-yl) ethylamine hydrochloride easily, so it is necessary to find a kind of convenient preparation method, so that a large amount of preparation 2-(1 -Methylimidazol-5-yl)ethylamine hydrochloride
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Embodiment 1
[0052] Preparation of 3-(Boc-amino)propanol (Ⅲ):
[0053] Dissolve 15Kg of 3-aminopropanol in 45L of dichloromethane, add 22.2Kg of triethylamine, stir and lower the temperature to 0-5°C, slowly add 45.8Kg of di-tert-butyl dicarbonate dropwise, and control the temperature not to exceed 10°C. After the addition, heat up to 20-25°C and react for 20 hours, add 30L of water, stir for 30 minutes, let stand to separate layers, extract the water layer with 15L of dichloromethane, combine the organic layers, wash with 30L of saturated brine, and dry over anhydrous sodium sulfate , filtered, and the filtrate was concentrated to dryness to obtain 33.6Kg of oily liquid 3-(Boc-amino)propanol, the purity of which was detected by GC was 98.9%, and the yield was 96.0%.
[0054] Preparation of 3-(Boc-amino)propanal (Ⅳ):
[0055] Dissolve 9.6Kg of oxalyl chloride in 100L of dichloromethane, lower the temperature of the reaction system to below -70°C, add dropwise 5.2Kg of dimethyl sulfoxide i...
Embodiment 2
[0061] Preparation of 3-(Boc-amino)propanol (Ⅲ):
[0062] Dissolve 15Kg of 3-aminopropanol in 45L of dichloromethane, add 22.2Kg of triethylamine, stir and lower the temperature to 0-5°C, slowly add 45.8Kg of di-tert-butyl dicarbonate dropwise, and control the temperature not to exceed 10°C. After the addition, heat up to 20-25°C and react for 20 hours, add 30L of water, stir for 30 minutes, let stand to separate layers, extract the water layer with 15L of dichloromethane, combine the organic layers, wash with 30L of saturated brine, and dry over anhydrous sodium sulfate , filtered, and the filtrate was concentrated to dryness to obtain 33.6Kg of oily liquid 3-(Boc-amino)propanol, the purity of which was detected by GC was 98.9%, and the yield was 96.0%.
[0063] Preparation of 3-(Boc-amino)propanal (Ⅳ):
[0064] Dissolve 9.6Kg of oxalyl chloride in 100L of dichloromethane, lower the temperature of the reaction system to below -70°C, add dropwise 5.2Kg of dimethyl sulfoxide i...
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Abstract
The invention discloses a new method for synthesizing 2-(1-methylimidazol-5-yl)ethylamine hydrochloride, comprising the following steps: step 1, using 3-aminopropanol as a starting material, and dicarbonic acid Di-tert-butyl ester reaction obtains 3-(Boc-amino) propanol; Step 2, Sven oxidation reaction: the obtained 3-(Boc-amino) propanol is obtained 3-(Boc-amino) propionaldehyde through Sven oxidation; step 3. Cyclization reaction: react the obtained 3-(Boc-amino) propionaldehyde with methylamine methanol solution to generate Schiff base, and directly react with p-toluenesulfonyl methyl isonitrile to synthesize 2-by Van Lesen reaction without separation (1-methyl-1H-imidazol-5-yl) tert-butyl ethyl carbamate; step 4, the obtained 2-(1-methyl-1H-imidazol-5-yl) ethyl carbamate tert-butyl The ester reacts with hydrogen chloride isopropanol solution to remove Boc to obtain the final product 2-(1-methylimidazol-5-yl)ethylamine hydrochloride. The beneficial effect of the present invention is that the present invention adopts the cheap and easy-to-obtain raw material to prepare, the reaction yield is high, the total steps are few, the operation is simple, the production cost is low, and it is easy to realize industrialization.
Description
technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a new method for synthesizing 2-(1-methylimidazol-5-yl)ethylamine hydrochloride. Background technique [0002] 2-(1-Methylimidazol-5-yl)ethylamine hydrochloride is an important intermediate of a new type of anticancer drug with broad application prospects. Although the synthetic patent report of this compound is used abroad, there are problems such as long steps and low yield. [0003] Patents US8618143, PCT2001009128, etc. disclose the synthesis of this compound, and the synthesis reaction equation of the patent US8618143 is as follows: [0004] [0005] In this method, due to the tautomerization of the amino hydrogen on the imidazole ring, the position of the methyl group cannot be fixed at the N-1 position, so the isomers of the compound (I) are produced, resulting in low yield and great difficulty in purification. Difficult to mass produce. [0006]...
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