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A pramoxine hydrochloride preparing method

A technology of pramoxine hydrochloride and pramoxine, which is applied in the field of pharmaceutical synthesis, can solve the problems of hydroquinone instability, no use found, and high environmental pressure, and achieve low cost, little pollution, and simple operation Effect

Inactive Publication Date: 2018-04-10
山东诚汇双达药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This route uses the raw material hydroquinone, which is easy to produce a by-product in the production process—p-phenylene dibutyl ether, and its use has not been found, and hydroquinone is unstable and easy to oxidize, the resulting wastewater has a darker color, and the treatment cost is higher , the pressure on environmental protection is relatively high

Method used

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Examples

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example 1

[0035] The preparation of intermediate p-bromobutyrate:

[0036] Add 17.47g (0.101mol) of p-bromophenol into a 250ml reaction flask, add 70g of water and 4.4g (0.11mol) of sodium hydroxide, stir to dissolve, add dropwise 13.7g (0.10mol) of 1-bromobutane, after the addition Heat up, reflux for 6 hours, cool down to 25°C, add 200ml of ethyl acetate, stop stirring after 10 minutes and let stand for liquid separation, wash twice with 100ml of 0.5% sodium hydroxide solution, dry with 20g of anhydrous sodium sulfate for more than 5 hours, 45 ℃ and concentrated to dryness under reduced pressure to obtain 23.2 g of a pale pink liquid with a yield of over 100 and a liquid phase purity of 98.5%.

[0037] Preparation of pramoxine hydrochloride:

[0038] Add 23.2g (0.1mol) of the above-mentioned intermediate, 17.42g (0.12mol) of 3-morpholine-1-propanol and 115g tetrahydrofuran into a 500ml reaction bottle, start stirring, slowly add 4.8g (0.12mol) of 60% sodium hydride, and control Temp...

example 2

[0040] The preparation of intermediate bromobutyrate:

[0041] Add 34.94g (0.202mol) of p-bromophenol into a 500ml reaction flask, add 140g of water and 8.8g (0.22mol) of sodium hydroxide, stir to dissolve, add dropwise 27.40g (0.20mol) of 1-bromobutane, after the addition Heat up, reflux for 6 hours, cool down to 25°C, add 200ml of ethyl acetate, stop stirring after 10 minutes, let stand for liquid separation, wash twice with 200ml of 0.5% sodium hydroxide solution, dry with 40g of anhydrous sodium sulfate for more than 5 hours, 45 ℃ and concentrated to dryness under reduced pressure to obtain 46.0 g of a pale pink liquid with a yield of over 100 and a liquid phase purity of 98.8%.

[0042] Preparation of pramoxine hydrochloride:

[0043] Add 46.0g (0.2mol) of the above-mentioned intermediate, 34.84g (0.24mol) of 3-morpholine-1-propanol and 230g tetrahydrofuran into a 1000ml reaction bottle, start stirring, slowly add 9.6g (0.24mol) of 60% sodium hydride, and control Temper...

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a pramoxine hydrochloride preparing method. The method includes reacting p-bromophenol and 1-bromobutaneunder catalytic functions of an alkali to prepare an intermediate that is 1-bromo-4-tert-butoxybenzene; synthesizing pramoxine having a base group from the 1-bromo-4-tert-butoxybenzene and 3-morpholinopropanol with the existence of a strong alkali; and subjecting the pramoxine having the base group to salification to obtain the pramoxine hydrochloride. The yield of the pramoxine hydrochloride prepared by the method is higher than 80%, and liquid-phase purity of the prepared pramoxine hydrochloride is higher than 99.8%. The method is used for preparing the pramoxine hydrochloride, and is simple to operate and high in yield, raw materials are easily available, product purity is high, the cost is low, and pollution is low.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a preparation method of pramoxine hydrochloride. Background technique [0002] Pramocaine hydrochloride (PRAMOXINE HYDROCHLORIDE), the chemical name is 4-(3-(4-butoxyphenoxy)propyl) morpholine hydrochloride, the molecular formula is C17H28ClNO3, the molecular weight is 329.86, and the structural formula is [0003] . [0004] Pramocaine is a non-paraben topical anesthetic. For patients who are allergic to other local anesthetics, the risk of cross-allergic reactions is minimized due to its special chemical structure. Pramocaine produces satisfactory topical anesthesia and is fairly well tolerated by the skin and non-delicate mucous membranes. [0005] In the prior art, the synthetic methods disclosed in the literature include: [0006] [0007] This route uses the raw material hydroquinone, which is easy to produce a by-product in the product...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 王素兰杨彦军孙宝亮胡俊峰李跃东
Owner 山东诚汇双达药业有限公司
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