CH237331A - Process for the preparation of diphenyl-morpholinoethyl-acetic acid ethyl ester. - Google Patents
Process for the preparation of diphenyl-morpholinoethyl-acetic acid ethyl ester.Info
- Publication number
- CH237331A CH237331A CH237331DA CH237331A CH 237331 A CH237331 A CH 237331A CH 237331D A CH237331D A CH 237331DA CH 237331 A CH237331 A CH 237331A
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenyl
- ethyl ester
- morpholinoethyl
- acetic acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- LQGIXNQCOXNCRP-UHFFFAOYSA-N dioxaphetyl butyrate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)CCN1CCOCC1 LQGIXNQCOXNCRP-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- -1 diphenyl morpholinoethyl - ethyl Chemical group 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 230000002048 spasmolytic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DPKWJKWZGPRUPI-UHFFFAOYSA-N 4-morpholin-4-yl-2,2-diphenylbutanenitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)CCN1CCOCC1 DPKWJKWZGPRUPI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung von Diphenyl-morpholinoäthyl-essigsäureäthylester. Gegenstand des vorliegenden Zusatzpatentes ist ein Verfahren zur Herstellung von Diphe- nylmorpholinoäthyl-essigsäureäthylester, wel ches dadurch gekennzeichnet ist, dass man N-Morpholino-äthylhalogenid auf Diphenyl- acetonitril in Gegenwart eines Halogenwas serstoff abspaltenden Mittels einwirken lässt und das so erhaltene basische Nitril in den zugehörigen Äthylester überführt.
<I>Beispiel:</I> 6 g Natriumamid in 100 cm' Benzol wer den mit 27 g Diphenylacetonitril und dann mit 22,5 g N-Morpholino-äthylchlorid umge setzt, wobei die im Hauptpatent angegebenen Bedingungen zugrunde gelegt werden. Nach dem Aufarbeiten und Umkristallisieren aus Hexahydrobenzol erhält man 28g Diphenyl- morpholinoäthyl-acetonitril als fast weisses Pulver vom Sinp. 82t .
<B>30</B> g Diphenyl-morpholinoäthyl-aceto- nitril werden mit 120 g 70%iger Schwefel säure unter den Bedingungen des Haupt patentes zur Säure verseift und die erhaltene Säure mit Äthylalkohol verestert. Nach der Aufarbeitung erhält man 24 g Diphenyl- morpholinoäthyl-essigsäureäthylester als dik- kes, fast farbloses Öl, das unter 4 mm Druck bei 218-222 siedet. Sein Chlorhydrat stellt farblose Kristalle dar, die bei 166 schmelzen.
Process for the preparation of diphenyl-morpholinoethyl-acetic acid ethyl ester. The subject of the present additional patent is a process for the preparation of Diphenylmorpholinoäthyl-acetic acid ethyl ester, wel Ches is characterized in that N-morpholino-ethyl halide is allowed to act on diphenyl acetonitrile in the presence of a hydrogen-releasing agent and the basic nitrile thus obtained in the associated ethyl ester transferred.
<I> Example: </I> 6 g of sodium amide in 100 cm of benzene are reacted with 27 g of diphenylacetonitrile and then with 22.5 g of N-morpholino-ethyl chloride, based on the conditions specified in the main patent. After working up and recrystallization from hexahydrobenzene, 28 g of diphenylmorpholinoethyl-acetonitrile are obtained as an almost white powder from Sinp. 82t.
<B> 30 </B> g of diphenylmorpholinoethyl acetonitrile are saponified with 120 g of 70% sulfuric acid under the conditions of the main patent and the acid obtained is esterified with ethyl alcohol. After working up, 24 g of diphenylmorpholinoethyl-acetic acid ethyl ester are obtained as a thick, almost colorless oil which boils at 218-222 under 4 mm pressure. Its chlorohydrate is colorless crystals that melt at 166.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE237331X | 1938-07-04 | ||
| CH231149T | 1939-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237331A true CH237331A (en) | 1945-04-15 |
Family
ID=25727561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237331D CH237331A (en) | 1938-07-04 | 1939-07-04 | Process for the preparation of diphenyl-morpholinoethyl-acetic acid ethyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237331A (en) |
-
1939
- 1939-07-04 CH CH237331D patent/CH237331A/en unknown
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