CH301585A - Process for the preparation of a new thioketopiperidine. - Google Patents
Process for the preparation of a new thioketopiperidine.Info
- Publication number
- CH301585A CH301585A CH301585DA CH301585A CH 301585 A CH301585 A CH 301585A CH 301585D A CH301585D A CH 301585DA CH 301585 A CH301585 A CH 301585A
- Authority
- CH
- Switzerland
- Prior art keywords
- thioketopiperidine
- ethyl
- new
- phenyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
verfahren zur Herstellung eines neuen Thioketopiperidins. (Tegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Thioketo- piperidins, welches dadurch gekennzeichnet ist, dass man 3-Phenyl-3-ät.hyl-2,6-dioxo- piperidin mit einem Sauerstoff durch Schwe fel ersetzenden l-Iittel behandelt.
Das so erhaltene 3-Pheny 1-3-äthyl-2-oxo-6- tliioketopiperidin der Formel
EMI0001.0011
vom F. = 73 bis 75 ist neu. Es besitzt anti- eonvulsive Wirksamkeit und soll als Heilmittel Verwendung finden.
Als Sauerstoff durch Schwefel ersetzendes Mittel verwendet man zweckmässig Phosphor- pentasulfid, vorzugsweise in Gegenwart eines Verdünnungsmittels, wie Pyridin.
Beispiel: 20 (Tewiehtsteile 3-Plienyl-3-ät.hyl-2,6-dioxo- l)iperidinwerden init120 Voluniteilenabsolutem Pyridin und 20 (lewichtsteilen fein pulverisier tem Pliospliorpentasulfid unter gutem Rühren während 2 Stunden am Rückfluss gekocht und hierauf das heisse Reaktionsgemisch in 1000 Volumteile heissen Wassers eingetragen.
Nach dem Abkühlen wird das Ganze mit Essigester eisschöpfend extrahiert, der Essigesterauszug mit verdünnter Sodalösung, verdünnter Salz- säure und schliesslich mit Wasser gewaschen, über Calciumchlorid getrocknet und das Lö sungsmittel abgedampft. Der Rückstand, be stehend aus 3-Phenyl-3-äthyl-2-oxo-6-thioketo- piperidin der Formel
EMI0001.0036
wird im Hochvakuum destilliert und geht über bei 159 bis 162 (0,12 mm).
Beim Stehen kri stallisiert diese Verbindung und zeigt, umkri stallisiert aus Essigester unter Zusatz von Ligroin, einen F. von 73 bis 75 .
process for the production of a new thioketopiperidine. (The subject matter of the present patent is a process for the production of a thioketopiperidine, which is characterized in that 3-phenyl-3-ethyl-2,6-dioxopiperidine is treated with a sulfur-replacing agent .
The 3-Pheny 1-3-ethyl-2-oxo-6-tliioketopiperidin of the formula obtained in this way
EMI0001.0011
vom F. = 73 to 75 is new. It has anti-eonvulsive effectiveness and is said to be used as a remedy.
The sulfur-replacing agent used is advantageously phosphorus pentasulfide, preferably in the presence of a diluent such as pyridine.
Example: 20 parts by weight of 3-plienyl-3-ethyl-2,6-dioxol) iperidine are refluxed with 120 parts by volume of absolute pyridine and 20 parts by weight of finely pulverized pliosplior pentasulfide with thorough stirring for 2 hours and then the hot reaction mixture in 1000 parts by volume of hot water entered.
After cooling, the whole thing is extracted with ice-scooping ethyl acetate, the ethyl acetate extract is washed with dilute soda solution, dilute hydrochloric acid and finally with water, dried over calcium chloride and the solvent is evaporated off. The residue, consisting of 3-phenyl-3-ethyl-2-oxo-6-thioketopiperidine of the formula
EMI0001.0036
is distilled in a high vacuum and goes over at 159 to 162 (0.12 mm).
This compound crystallizes on standing and shows, umkri crystallized from ethyl acetate with the addition of ligroin, a F. of 73 to 75.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH301585T | 1952-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301585A true CH301585A (en) | 1954-09-15 |
Family
ID=4491095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301585D CH301585A (en) | 1952-04-03 | 1951-04-28 | Process for the preparation of a new thioketopiperidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301585A (en) |
-
1951
- 1951-04-28 CH CH301585D patent/CH301585A/en unknown
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