CH199677A - Process for the preparation of 2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine. - Google Patents
Process for the preparation of 2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine.Info
- Publication number
- CH199677A CH199677A CH199677DA CH199677A CH 199677 A CH199677 A CH 199677A CH 199677D A CH199677D A CH 199677DA CH 199677 A CH199677 A CH 199677A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydropyridine
- diethyl
- dioxo
- bromo
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- VRECPHBGAYOAML-UHFFFAOYSA-N 5-bromo-3,3-diethylpiperidine-2,4-dione Chemical compound O=C1NCC(C(C1(CC)CC)=O)Br VRECPHBGAYOAML-UHFFFAOYSA-N 0.000 title 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- NZASCBIBXNPDMH-UHFFFAOYSA-N 3,3-diethyl-1H-pyridine-2,4-dione Chemical compound CCC1(CC)C(=O)NC=CC1=O NZASCBIBXNPDMH-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2,4-Diogo-3,3-diäthyl-5-brom-tetrahydropyridin. Es wurde gefunden, dass durch die Ein wirkung halogenierend wirkender Mittel auf 2,4-Diogo-3,3-dialkyl-tetrahydropyridine in glatt verlaufender Umsetzung der Wasser stoff in der 5-Stellung durch Halogen sub stituiert werden kann. Mit den 1- oder 6- Methyl- bezw. 1,6 - Dimethylverbindungen verläuft die Umsetzung durchaus gleichsin nig und führt zu gleichartigen Verbindun gen.
Die Ausgangsstoffe gewinnt man nach den Verfahren des schweizerischen Patentes Nr. 187826 und seiner Zusätze, sowie der deutschen Patente Nr. 637385 und Nr. 638532. Es ist überraschend, dass bei diesen Umset zungen Substitution erfolgt und nicht Addi tion. Man kann darin auch kein dem Pyri- din ähnliches Verhalten erblicken, denn die Halogenierungen verlaufen rasch und glatt unter sehr milden Bedingungen. Diese wer den deshalb vorzugsweise bei niedrigen Tem peraturen unter Anwendung von Lösungs mitteln vorgenommen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 2,4-Diogo- 3,3-diäthyl-5-bromtetrahydropyridin, welches dadurch gekennzeichnet ist, dass auf 2,4 Diogo - 3,3 - diäthyltetrahydropyridin Brom einwirken gelassen wird.
Das neue 2,4-Diogo-3,3-diäthyl-5-brom- tetrahydropyridin bildet blass gelbliche Na deln, die bei 111 bis 112 schmelzen und in den gebräuchlichen organischen Lösungsmit teln leicht löslich sind. In wässerigen Alka- lien löst sich die Verbindung unverändert mit gelblicher Farbe. Sie wirkt schlaf machend und soll als Arzneimittel verwen det werden.
<I>Beispiel:</I> 167 Gewichtsteile 2,4-Diogo-3,3-diäthyl- tetrahydropyridin werden unter Rühren in 700 Volumenteilen Methylenchlorid gelöst. Zu dieser Lösung lässt man unter fortgesetz tem Rühren eine Lösung von 160 Gewichts teilen Brom in 300 Volumteilen Methylen- chlorid langsam zufliessen. Die Temperatur wird zwischen 5 und 15 gehalten. Das Brom verschwindet sofort. Bald beginnt Bromwasserstoff zu entweichen.
Nachdem alles Brom zugetropft ist, wird das Methy- lenchlorid verdampft. Das 2,4 - Dioxo - 3,3- diäth\#1-5-brom-tetrahydropyridin bleibt als feste Masse zurück. Es wird zur Reinigung beispielsweise aus Benzol unter Zusatz von wenig Petroläther umkristallisiert.
Process for the preparation of 2,4-diogo-3,3-diethyl-5-bromo-tetrahydropyridine. It has been found that the action of halogenating agents on 2,4-diogo-3,3-dialkyl-tetrahydropyridines can be substituted for the hydrogen in the 5-position by halogen in a smooth reaction. With the 1- or 6- methyl- respectively. 1,6-dimethyl compounds, the reaction proceeds in the same way and leads to similar compounds.
The starting materials are obtained by the process of Swiss patent No. 187826 and its additives, and German patents No. 637385 and No. 638532. It is surprising that in these conversions there is substitution and not addition. Nor can one see any behavior similar to that of pyridine, since the halogenations proceed quickly and smoothly under very mild conditions. These who are therefore preferably made at low temperatures using solvents.
The subject of the present patent is a process for the preparation of 2,4-diogo-3,3-diethyl-5-bromotetrahydropyridine, which is characterized in that bromine is allowed to act on 2,4-diogo-3,3-diethyltetrahydropyridine.
The new 2,4-diogo-3,3-diethyl-5-bromo-tetrahydropyridine forms pale yellowish needles that melt at 111 to 112 and are easily soluble in common organic solvents. In aqueous alkali the compound dissolves unchanged with a yellowish color. It has a sleep-inducing effect and is intended to be used as a medicine.
<I> Example: </I> 167 parts by weight of 2,4-diogo-3,3-diethyl-tetrahydropyridine are dissolved in 700 parts by volume of methylene chloride with stirring. A solution of 160 parts by weight of bromine in 300 parts by volume of methylene chloride is allowed to flow slowly into this solution, with continued stirring. The temperature is kept between 5 and 15. The bromine disappears immediately. Soon hydrogen bromide begins to escape.
After all the bromine has been added dropwise, the methylene chloride is evaporated. The 2,4-dioxo-3,3-diet 1-5-bromo-tetrahydropyridine remains as a solid mass. For cleaning, it is recrystallized from benzene, for example, with the addition of a little petroleum ether.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199677X | 1936-04-25 | ||
| CH193773T | 1937-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199677A true CH199677A (en) | 1938-08-31 |
Family
ID=25722576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199677D CH199677A (en) | 1936-04-25 | 1937-02-26 | Process for the preparation of 2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199677A (en) |
-
1937
- 1937-02-26 CH CH199677D patent/CH199677A/en unknown
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