CH222485A - Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isobutyl-ketone. - Google Patents
Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isobutyl-ketone.Info
- Publication number
- CH222485A CH222485A CH222485DA CH222485A CH 222485 A CH222485 A CH 222485A CH 222485D A CH222485D A CH 222485DA CH 222485 A CH222485 A CH 222485A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- methyl
- isobutyl
- piperidyl
- ketone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- -1 isobutylmagnesium halide Chemical class 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZSGJKBKUYXDVIE-UHFFFAOYSA-N CC(C)C[Mg] Chemical compound CC(C)C[Mg] ZSGJKBKUYXDVIE-UHFFFAOYSA-N 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N Isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- KHUPPYUUMRDAAX-UHFFFAOYSA-N Pethidinic acid Chemical compound C1CN(C)CCC1(C(O)=O)C1=CC=CC=C1 KHUPPYUUMRDAAX-UHFFFAOYSA-N 0.000 description 1
- YUPZOKFCNKSJTR-UHFFFAOYSA-M [Cl-].CC(C)C[Mg+] Chemical compound [Cl-].CC(C)C[Mg+] YUPZOKFCNKSJTR-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
Verfahren zur Herstellung von 1-Methyl-4-phenyl-piperidyl-4-isobutyl-keton. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Herstellung von 1-Methyl-4-phenyl-piperidyl-4-isobutyl- keton, welches dadurch gekennzeichnet ist, dass man auf 1-Methyl-4-phenyl-piperidin- 4-carbonsäurenitril Isobutylmagnesiumhalo- genid einwirken lässt und das entstandene Ketimidzwischenprodukt mit verdünnter Säure zerlegt.
Das 1-Methyl-4-phenyl-piperidyl-4-iso- butyl-keton ist ein farbloses<B>01</B> vom Kpzi 155-160'. Es soll für pharmazeutische Zwecke Verwendung finden. Das Phosphat ist ein farbloses Kristallpulver vom F. 166 bis 167 .
Beispiel: Eine Isobutylmagnesiumchlori:dlösung, aus 46 Gewichtsteilen Isobutylchlorid und 12 Ge wichtsteilen Magnesium in 150 Gewichtstei len Äther bereitet, wird zu einer Lösung von 60 Gewichtsteilen 1-Methyl-4-phenyl-piperi- din-4-carbonsäurenitril in 100 Gewichtsteilen Toluol zugesetzt. Die auftretende Reaktions wärme ist nicht erheblich; nach ihrem Ab klingen wird das Gemisch auf dem Wasser bade am absteigenden Kühler erhitzt; der Äther destilliert ab, die Toluollösung wird drei Stunden bei Wasserba.dtemperatur ge halten.
Die Zerlegung erfolgt durch Auf giessen auf Eis und Verrühren mit verdünn ter Salzsäure, von der so viel anzuwenden ist, dass kongosaure Reaktion auf die Dauer be stehen bleibt. Nach Abtrennung des Toluods fällt man die Base durch Übersättigen, der wässerigen Lösung mit Ammoniak als 01 aus, nimmt sie in Äther auf, trocknet über Kaliumcarbonat und destilliert. Kp, 155 bis <B>160'.</B> Die Base ist ein farbloses Öl. Das aus der Base mit 1 Mol Phosphorsäure in wässe riger Lösung erhältliche Phosphat kristalli siert in farblosen Kristallen vom F. 166 bis 167 .
Es ist mässig leicht löslich in kaltem, leicht löslich in heissem Wasser. Die Lösung reagiert lackmussauer.
Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isobutyl-ketone. The subject of the present additional patent is a process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isobutyl ketone, which is characterized in that 1-methyl-4-phenyl-piperidine-4-carboxylic acid nitrile isobutylmagnesium Genid is allowed to act and the resulting ketimide intermediate is broken down with dilute acid.
The 1-methyl-4-phenyl-piperidyl-4-isobutyl-ketone is a colorless 01 of the Kpzi 155-160 '. It is said to be used for pharmaceutical purposes. The phosphate is a colorless crystal powder from F. 166 to 167.
Example: An isobutylmagnesium chloride solution, prepared from 46 parts by weight of isobutyl chloride and 12 parts by weight of magnesium in 150 parts by weight of ether, is added to a solution of 60 parts by weight of 1-methyl-4-phenyl-piperidine-4-carboxylic acid nitrile in 100 parts by weight of toluene . The resulting reaction heat is not significant; after they sound off, the mixture is heated on the water bathing on the descending cooler; the ether distills off and the toluene solution is kept at water temperature for three hours.
It is broken down by pouring it onto ice and stirring it with dilute hydrochloric acid, of which so much has to be used that the Congo acidic reaction lasts for a long time. After separating off the toluod, the base is precipitated by supersaturation of the aqueous solution with ammonia as oil, it is taken up in ether, dried over potassium carbonate and distilled. Kp, 155 to <B> 160 '. </B> The base is a colorless oil. The phosphate obtainable from the base with 1 mol of phosphoric acid in aqueous solution crystallizes in colorless crystals with a melting point of 166 to 167.
It is moderately easily soluble in cold, slightly soluble in hot water. The solution reacts lackluster.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE222485X | 1939-03-30 | ||
| CH218517T | 1940-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH222485A true CH222485A (en) | 1942-07-15 |
Family
ID=25726172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH222485D CH222485A (en) | 1939-03-30 | 1940-03-30 | Process for the preparation of 1-methyl-4-phenyl-piperidyl-4-isobutyl-ketone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH222485A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486796A (en) * | 1943-06-25 | 1949-11-01 | Ciba Pharm Prod Inc | Esters of 1-alkyl-4-hydroxyphenylpiperidyl-4-ketones |
-
1940
- 1940-03-30 CH CH222485D patent/CH222485A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486796A (en) * | 1943-06-25 | 1949-11-01 | Ciba Pharm Prod Inc | Esters of 1-alkyl-4-hydroxyphenylpiperidyl-4-ketones |
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