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Preparation method of phenoxybenzamine hydrochloride

A technology of phenoxybenzamine hydrochloride and benzyl, which is applied in the field of medicine and can solve problems such as hidden dangers in production safety, low reaction yields, unfavorable applications, etc.

Active Publication Date: 2013-11-27
SUZHOU HOMESUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this route, thionyl chloride is used twice, so that the overall reaction yield will be low, and at the same time, there will be hidden dangers for safe production, which is not conducive to large-scale application

Method used

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  • Preparation method of phenoxybenzamine hydrochloride
  • Preparation method of phenoxybenzamine hydrochloride
  • Preparation method of phenoxybenzamine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108]

[0109] Add 500 milliliters of water into the reaction vessel, dissolve 188 grams of phenol therein, and stir evenly with a mechanical stirrer. Slowly add 160 grams of sodium hydroxide again, add 139 grams of methyl oxirane after stirring evenly. Reacted for 8 hours under the condition of 45 degrees. After the reaction, cool in an ice-water bath, filter to remove incompatible impurities, then extract the filtrate with ethyl acetate, take the organic layer, evaporate the solvent under reduced pressure, wash, and dry to obtain a colorless liquid 1-phenoxy-2- Hydroxypropane 292 grams, HPLC purity analysis>99%, product yield is 95%. IR (Neat, cm -1 ):νmax 3063,3003,2926,1595,1496,1456,1346,1296,1244,1174,1080,1039,914,860,758,692; l H NMR (400MHz, CDCl 3 ):δ2.72-2.76(dd,J=5.0,2.0Hz),2.86-2.91(t,J=5.0Hz,1H),3.30-3.38(m,1H),3.89-3.97(dd,J=11.0 ,6.0Hz,1HZ),4.17–4.24(dd,J=11.0,4.0Hz,1H),6.89–7.0(m,3H),7.24–7.33(m,2H); 13 C NMR (100MHz, CDCl 3 ): δ158.4, 129.4, 121.1,...

Embodiment 2

[0123] In the step (1), the alkali is potassium carbonate, and the molar amount of the alkali is twice that of phenol. The rest are the same as step (1) in the first embodiment. 198 grams of 1-phenoxy-2-hydroxypropane was obtained as a colorless liquid, the HPLC purity analysis was >99%, and the product yield was 65%.

Embodiment 3

[0125] In the step (1), the alkali is sodium carbonate, and the molar amount of the alkali is twice that of phenol. The rest are the same as step (1) in the first embodiment. Obtained 218 grams of colorless liquid 1-phenoxy-2-hydroxypropane, HPLC purity analysis>99%, product yield was 71%.

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Abstract

The invention relates to a preparation method of phenoxybenzamine hydrochloride, which comprises the following steps: reacting phenol with methyl epoxyethane to obtain 1-phenoxy-2-hydroxy propane; reacting 2-nitrobenzenesulfonyl chloride with benzylamine to obtain N-2-nitrobenzenesulfonyl benzylamine; reacting the obtained 1-phenoxy-2-hydroxy propane with the N-2-nitrobenzenesulfonyl benzylamine to obtain N-benzyl-N-(1-methyl-2-phenoxyethyl)-2-nitro-benzsulfamide; converting the N-benzyl-N-(1-methyl-2-phenoxyethyl)-2-nitro-benzsulfamide into N-(1-methyl-2-phenoxyethyl) benzylamine; reacting the obtained N-(1-methyl-2-phenoxyethyl) benzylamine with 2-bromoethanol to obtain benzyl-(1-methyl-2-phenoxyethyl) ethanol; and dissolving benzyl-(1-methyl-2-phenoxyethyl) ethanol in a solvent, introducing hydrogen chloride gas, dropwisely adding thionyl chloride, and performing reflux reaction to obtain phenoxybenzamine hydrochloride.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of phenoxybenzamine hydrochloride. Background technique [0002] Phenoxybenzamine hydrochloride is a drug used to treat urinary retention caused by peripheral vasospasm disease and benign prostatic hyperplasia (see: Zou Aiping, Wang Difu, Wu Feng. Journal of Wuhan Medical College, 1984, 4, 282-285), it can Changing the vasoconstriction response due to the excitation of α-receptors can reduce the resistance of peripheral blood vessels and the ability to relieve the capacity of blood vessels in a constricted state, thereby increasing the volume of blood vessels by 20%-30%. It has the ability to increase myocardial contractility, increase heart rate and lower blood pressure, reduce peripheral vascular resistance, increase cardiac output and reduce oxygen consumption (see: A.Kulik, F.Rubens, D.Gunni ng, M .Bourke, M.Ruel.The Annals of Thoracic Surgery, 2007,83,509), in a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/16C07C213/08
Inventor 杨颖瑾
Owner SUZHOU HOMESUN PHARMA