PL652B1 - The method of obtaining an aryl α-dialkylamino ester ester. p-oxyma, - Google Patents
The method of obtaining an aryl α-dialkylamino ester ester. p-oxyma, Download PDFInfo
- Publication number
- PL652B1 PL652B1 PL652A PL65221A PL652B1 PL 652 B1 PL652 B1 PL 652B1 PL 652 A PL652 A PL 652A PL 65221 A PL65221 A PL 65221A PL 652 B1 PL652 B1 PL 652B1
- Authority
- PL
- Poland
- Prior art keywords
- ester
- aryl
- obtaining
- oxyma
- dialkylamino
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- -1 ketone acids Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Description
Wykryto, ze estry aromatyczne estru kwasu a-dwualkilo-amino-etylo-(3-oksyma- slowego o wzorze ogólnym: CHZ -CH — CH — COOR I I OH — CH2—CH2 — NR2 (w którym R oznacza 2 alkile lub 1 alkil, jak np. pentametylen), otrzymywane przez redukcje odpowiednich kwasów ketonowych i nastepnie estryfikowane arylem zapomoca kwasów aromatycznych dzialaja znieczulajaco, dzieki czemu moga znalesc zastosowanie w medycynie. Jako produkt wyjsciowy sluza estry zasadowe kwasów ketonowych, otrzymywane zapo¬ moca polaczenia chlorowca dwualkilo- aminoetylu z pochodna sodowa estru acetylooctowego, np., przez redukcje za¬ pomoca orteci sodowej przechodza one w pochodne kwasu (3-oksymaslowego.Otrzymywany np. przez redukcje estru kwasu a-dwuetyloaminoetyloacetyloocto- wego ester kwasu a - dwuetyloamino- P-oksymaslowego jest ciecza bezbarwna, wrzaca w 135°— 136° C (p = 10 mm), rozpuszczalna w wodzie o odczynie za¬ sadowym; jest on równiez latwo roz¬ puszczalny w alkoholu i eterze.Przyklad. 115 czesci estru kwasu a-dwuetylo- aminoetylo-p-oksymaslowego i 80 czesci chlorku benzoylu rozpuszcza sie w 80 cze¬ sciach benzolu, miesza i nagrzewa 1—2 go¬ dzin na lazni wodnej. Produkt reakcji wyklóca sie dokladnie woda, oddziela od benzolu i osadza z przesaczonego roztworu wodnego zapomoca alkalji ben- zoylowany ester kwasu a-dwuetyloami- noetylooksymaslowego. Zasade wyciagasie eterem; pozostaly po odpedzeniu eteru olej, prawie bezbarwny, jest w wo¬ dzie nierozpuszczalny, lecz rozpuszczalny latwo w rozpuszczalnikach organicznych, jak: eter, alkohol, benzol. Otrzymany przez zobojetnienie kwasem solnym chlo¬ rowodorek krystalizuje sie z acetonu w postaci pieknych igiel bezbarwnych, topniejacych w 130°—131° C. Sól ta jest latwe rozpuszczalna w wodzie, da¬ jac odczyn obojetny. Alkalja osadzaja zasade w postaci oleju. PL PLAromatic esters of α-dialkylamino-ethyl- (3-oxybaldehyde) with the general formula: CHZ -CH - CH - COOR II OH - CH2-CH2 - NR2 (where R is 2 alkyl or 1 alkyl) have been found , e.g. pentamethylene), obtained by reduction of appropriate ketone acids and then esterified with aryl with aromatic acids, have an anesthetic effect, so that they can be used in medicine. Basic esters of ketone acids serve as the starting product, obtained by combining dialkyl aminoethyl halogen with the sodium derivative of the acetoacetic ester, for example, by reduction with sodium orthhex, they are converted into derivatives of (3-oxybutyric acid. The α-diethylaminoethylacetylacetic acid ester obtained, for example, by reduction of the α-diethylamino-β-oxybutyric acid ester, is a colorless liquid. boiling at 135 ° - 136 ° C (p = 10 mm), soluble in alkaline water; it is also easily soluble in alcohol and ether. Example 115 parts of acid ester ad wuethyl-aminoethyl-p-oxybutyric acid and 80 parts of benzoyl chloride are dissolved in 80 parts of benzol, mixed and heated for 1-2 hours in a water bath. The reaction product is lined up with exactly water, separated from the benzol and deposited from the filtered aqueous solution by means of an alkali benzoylated ester of α-diethylaminoethyl oxybutyric acid. Principle is drawn out with ether; the oil remaining after the ether has been stripped off, which is almost colorless, is insoluble in water, but easily soluble in organic solvents such as ether, alcohol, benzene. The hydrochloride obtained by neutralization with hydrochloric acid crystallizes from acetone in the form of beautiful, colorless needles, melting at 130 ° -131 ° C. This salt is easily soluble in water, making it neutral. Alkali deposit the base as an oil. PL PL
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Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL652B1 true PL652B1 (en) | 1924-10-31 |
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