SU358932A1

SU358932A1 - Method for preparing phenylacetic acid diethylaminoethyl ester

Info

Publication number: SU358932A1
Application number: SU1479363A
Authority: SU
Inventors: А.Н. Высокосов; И.А. Высокосова; А.В. Беликин; Р.Л. Глобус
Original assignee: Московский Химический Завод Им.Войкова
Priority date: 1970-10-01
Filing date: 1970-10-01
Publication date: 1976-02-25

Description

(54) СПОСОБ ПОЛУЧЕНИЯ ДИЭТИЛАМИНОЭТИЛОВОГО ЭФИРА (54) METHOD OF OBTAINING DIETHYLAMINOETHYL ETHER

Изобретение относитс к способам получени сложных эфиров фенилуксусной кислоты , а именно диэтиламиноэтилового эфира фенилуксусной кислоты, который может найти применение в качестве физиологически активных веществ.This invention relates to methods for producing phenylacetic acid esters, namely, phenylacetic acid diethylaminoethyl ester, which can be used as physiologically active substances.

Известен способ получени диэтиламиноэтилового эфира фенилуксусной кислоты пере этерификацией сложного эфира низшего спирта и фенилуксусной кислоты с диэтиламиноэтанолом в присутствии катализатора - эти- лата натри . Однако такой катализатор в ходе реакции быстро пассивируетс (видимо, вступает в побочные реакции), поэтому дл зaвepшt.lIи процесса его необходимо вводить повторно. Кроме того, такой катализатор вызывает образование высококип$ццих примесей . Все это приводит к увеличению времени реакции, снижению выхода (около 8О%) и ухудшению качества целевого продукта.A known method for preparing phenylacetic acid diethylaminoethyl ester is by re-esterifying a lower alcohol and phenylacetic acid ester with diethylaminoethanol in the presence of a sodium ethylate catalyst. However, such a catalyst is quickly passivated during the reaction (apparently, it enters into side reactions), therefore, it is necessary to re-enter it to complete the process. In addition, such a catalyst causes the formation of high-boiling impurities. All this leads to an increase in reaction time, a decrease in yield (about 8O%) and a deterioration in the quality of the target product.

С целью устранени указанных недостагков по предлагаемому способу в качестве катализатора используют алкогол ты менее активных щелочноземельных металлов, которые не вызывают указанных побочных проФЕНИЛУКСУСНОЙ КИСЛОТЫIn order to eliminate the indicated deficiencies in the proposed method, alcohols of less active alkaline earth metals are used as a catalyst, which do not cause the indicated side pro-phenylacetic acid

цессов, не пассивируютс и позвол ют быстро достигать практически почти количоствонных превращений этилового эфира и диэтиламиноэтиловый эфир фенилуксусной кислоты хорошего Качества.These processes are not passivated and allow you to quickly achieve almost almost quantitative transformations of ethyl ether and diethylaminoethyl ether of phenylacetic acid of good Quality.

Образующиес в ходе реакции низкокип щий спирт непрерывно удал ют отгонкой на небольшой колонке. Вместо этилового эфира фенилуксусной кислоты можно использовать метиловый, пропиловый, изопропиловый и другие доступные эфиры низкокип тих спиртов. В качестве катализатора из шелочноземальных металлов наиболее удобен в работе магний , который можно вводить в реактор в виде свободного металла или даже в виде окиси . Во всех этих случа х он образует с диэтиламиноэтанолом алкогол т, который вл етс катализатором.The low boiling alcohol formed during the reaction is continuously removed by distillation on a small column. Methyl, propyl, isopropyl and other low boiling esters of these alcohols can be used instead of phenylacetic acid ethyl ester. As a catalyst from the silo-earth metals, magnesium is most convenient in operation, which can be introduced into the reactor as a free metal or even as an oxide. In all these cases, it forms an alcoholate with diethylaminoethanol, which is a catalyst.

Claims

Example 1. A mixture of 11OO g (6.7 g-mol) of phenylacetic acid ethyl ester, 1600 g (13.6 g-mole) of diethylaminoethanol and 1.6 g of metallic magnesium are heated to a low boil (about 180 in a bath) in a flask Packed column (not a column of 2 O-25 cm) with adjustable gate phlegm. In this case, the fraction boiling under TSt is distilled off. After about 20 O-250 ml of ethanol, the temperature in the vapor rises. The distillation of the first fraction are up to 100 ° C. iOsa contains ethanol with a small admixture of diphylpminoethanol. 11 a vacuum of about 2 mm of mercury is created. Art. and excess diethylaminoethanol is distilled off. The residue is distilled in vacuo to discolor or used for further purposes without distillation. The content of the basic substance in the un-distilled end product is about 99%. The catalyst is precipitated from the product and can be removed by filtration. The output is almost quantitative. EXAMPLE 2 The process is carried out analogously to Example 1, but instead of ethyl ester, the same molar amounts of methyl, propyl, isopropyl, butyl, isobutyl, I-butyl, ter-p-butyl esters of phenylacetic acid, C are used. with higher boiling alcohols, the reaction also proceeds fairly easily, but the separation of the first and second fractions is less clear, which may make it difficult to reuse them in arbitrariness. The impurity content in the target product is also increased. EXAMPLE 3. The process is carried out as in Example 1, but about 2 g of magnesium oxide is added instead. The results are the same as in Example 1. EXAMPLE 4. The process is carried out as in Example 2, but magnesium oxide is used instead of metallic magnesium. The results do not differ much from the example.

2. The invention The method of obtaining the phenylacetic acid diethylaminoate ester by transesterifying the lower alcohol ester of phenylacetic acid with diethylaminoethanol in the presence of a catalyst - an alcoholic metal, followed by isolating the target product by known methods, is asymptomatic, and an alumina metal is used, followed by the extraction of the target product by known methods, in the presence of a catalyst of an alcoholic metal, followed by the separation of the target product by known methods, in the presence of an alcoholic metal, followed by the addition of an alcohol of the metal, followed by the separation of the target product by known methods, and in the presence of an alcoholic metal with the subsequent treatment the aim is to increase the yield and improve the quality of the target product; alkaline earth metal is used as the catalyst for the oxide.