SU52447A1 - The method of obtaining diethyl-amino-propyl ether - Google Patents
The method of obtaining diethyl-amino-propyl etherInfo
- Publication number
- SU52447A1 SU52447A1 SU52447A1 SU 52447 A1 SU52447 A1 SU 52447A1 SU 52447 A1 SU52447 A1 SU 52447A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- diethyl
- quinoline
- phenyl
- propyl ether
- Prior art date
Links
- -1 diethyl-amino-propyl ether Chemical compound 0.000 title description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-N,N-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 4
- YTRMTPPVNRALON-UHFFFAOYSA-N Cinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229940072033 potash Drugs 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003247 radioactive fallout Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 1
- 230000003444 anaesthetic Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XMVYZYSRFLFCCS-UHFFFAOYSA-N propyl 2-phenylquinoline-4-carboxylate Chemical compound N=1C2=CC=CC=C2C(C(=O)OCCC)=CC=1C1=CC=CC=C1 XMVYZYSRFLFCCS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ZSOINCKGNIMAEG-UHFFFAOYSA-M sodium;2-phenylquinoline-4-carboxylate Chemical compound [Na+].N=1C2=CC=CC=C2C(C(=O)[O-])=CC=1C1=CC=CC=C1 ZSOINCKGNIMAEG-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Насто щее изобретение относитс к методу получени диэтил-амино-пропилового эфира 2-фенил-хинолин4-карбоновой кислоты. Сол нокисла соль этого соединени обладает анестезирующими свойствами, испытанными в клинике на животных.The present invention relates to a method for preparing 2-phenyl-quinoline-4-carboxylic acid diethyl-amino-propyl ester. Soloxide salt of this compound has anesthetic properties tested in animal clinics.
Автор насто щего изобретени нашел , что указанный выще продукт может быть получен нагреванием в каком-либо органическом растворителе натриевой соли 2-фенил-хинолин-4-карбоновой кислоты с диэтиламино-пропил-хлоридом . После проведени конденсации получаетс диэтиламино-пропиловый эфир 2-фенил-хинолин-4-карбоновой кислоты.The inventor has found that the above product can be obtained by heating the sodium salt of 2-phenyl-quinoline-4-carboxylic acid with diethylamino-propyl chloride in some organic solvent. After condensation, 2-phenyl-quinoline-4-carboxylic acid diethylaminopropyl ester is obtained.
Пример 1.Example 1
10 г натриевой соли 2-фенил-хинолин4-карбоновой кислоты суспендируют в 150 г сухого ксилона. В суспенз внос т 7 г свеже перегнанного диэтиламино-пропил-хлорида и смесь кип т т в течение 7 часов. По окончании нагревани реакционную массу фильтруют; на фильтре остаетс поваренна соль, а в фипьтрате-диэтил-аминопропиловый эфир 2-фенил-хинолин4-карбоновой кислоты. Ксилольный раствор промывают 2%-м водным раствором поташа, затем водой, после чего прибавл ют вычисленное количество сол ной кислоты. Выпадают белые кристаллы сол нокислой соли диэтил-амино-пропилового эфира 2-фенил-хинолин - 4 - карбоновой кислоты. Кристаллы отфильтровывают и перекристаллизовывают из 5-кратного количества спирта. Температура плавлени полученного продукта 175- 176°.10 g of the sodium salt of 2-phenyl-quinoline-4-carboxylic acid are suspended in 150 g of dry xylene. 7 g of freshly distilled diethylamino-propyl chloride are introduced into the suspension and the mixture is boiled for 7 hours. At the end of the heating, the reaction mass is filtered; the salt remains on the filter, and 2-phenyl-quinoline-4-carboxylic acid in the dietary-diethyl-aminopropyl ester. The xylene solution is washed with a 2% aqueous solution of potash, then with water, after which the calculated amount of hydrochloric acid is added. White crystals of the hydrochloric acid salt of 2-phenyl-quinoline-4-carboxylic acid diethyl-amino-propyl ester fall out. The crystals are filtered and recrystallized from 5-fold amount of alcohol. Melting point of the obtained product is 175-176 °.
П р и ме р 2.PRI me p 2.
10 г натриевой соли 2-фенил-хинолин-4-карбоновой кислоты суспендируют в 150 г сухого ксилола. Б суспенз внос т 12 г сол нокислой соли диэтил-амино-пропил-хлорида, 3 г прокаленного поташа и несколько кубических сантиметров спирта. Реакционную смесь нагревают 12-15 часов, образовавшийс осадок отфильтровывают и раствор ют в сол ной кислоте. Сол нокислый раствор фильтруют, приливают к нему раствор поташа до щелочной реакции и экстригируют эфиром. К высушенной эфирной выт жке приливают вычисленное количество спиртового раствора хлористого водорода; ьыпадают белые кристаллы, их отфильтровывают и10 g of sodium salt of 2-phenyl-quinoline-4-carboxylic acid are suspended in 150 g of dry xylene. 12 g of hydrochloric salt of diethyl-amino-propyl chloride, 3 g of calcined potash and a few cubic centimeters of alcohol are added to the suspension. The reaction mixture is heated for 12-15 hours, the precipitate formed is filtered and dissolved in hydrochloric acid. The hydrochloric acid solution is filtered, the solution of potash is added to it until alkaline, and it is extracted with ether. A calculated amount of an alcoholic solution of hydrogen chloride is added to the dried ethereal extract; white crystals fall out, they are filtered and
перекристаллизовывают из спирта, после чего они плав тс при 175- 176recrystallized from alcohol, after which they melt at 175- 176
Предмет изобретени .The subject matter of the invention.
Способ получени диэтил-амино (пропилового эфира 2-фенил-хинолин4-карбоновой кислоты, отличающийс тем, что натриевую соль 2-фенилхинолин-4-карбоновой кислоты нагревают в каком-либо органическом растворителе с диэтил-амино-пропил-хлоридом или его сол нокислой солью и полученный продукт обрабатывают далее обычными методами.A method for preparing diethyl-amino (2-phenyl-quinoline-4-carboxylic acid propyl ester, characterized in that the 2-phenyl-quinoline-4-carboxylic acid sodium salt is heated in an organic solvent with diethyl-amino-propyl-chloride or its hydrochloric acid salt and the resulting product is further processed by conventional methods.
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