CH199680A - Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine. - Google Patents
Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine.Info
- Publication number
- CH199680A CH199680A CH199680DA CH199680A CH 199680 A CH199680 A CH 199680A CH 199680D A CH199680D A CH 199680DA CH 199680 A CH199680 A CH 199680A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- tetrahydropyridine
- dioxo
- propyl
- bromo
- Prior art date
Links
- PFZOWUIFRZJTNR-UHFFFAOYSA-N O=C1NC(C(C(C1(CCC)CCC)=O)Br)C Chemical compound O=C1NC(C(C(C1(CCC)CCC)=O)Br)C PFZOWUIFRZJTNR-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 2,4-dioxo-3,3-di - n - propyl - 6 - methyl-tetrahydropyridine bromine Chemical compound 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 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 group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 2,4-Diogo-3,3-di-n-propyl-5-brom-6-methyl- tetrahydropyr idin. Es wurde gefunden, dass :durch die Ein wirkung halogenierend wirkender Mittel auf 2,4-Dioxo-3,3-dialkyl-tetrahydropyrid-ine in glatt verlaufender Umsetzung der Wasser stoff in der 5-.Stellung durch Halogen sub stituiert werden kann.
Mit den 1- oder 6-Me- thyl- bezw. 1,6-Dimethylverbindungen ver läuft die Umsetzung durchaus .gleichsinnig und führt zu gleichartigen Verbindungen. Die Ausgangsstoffe gewinnt man nach den Verfahren des schweizerischen Patentes Nr.187826 und seiner Zusätze, sowie der deutschen Patente Nr.637385 und 63$532, Es ist überraschend, dass bei diesen Um setzungen Substitution erfolgt und nicht Addition.
Man kann darin auch kein dem Pyridin ähnliches Verhalten erblicken, denn die Halogenierungen verlaufen rasch und glatt unter sehr milden Bedingungen. Diese werden deshalb vorzugsweise bei niedrigen Temperaturen unter Anwendung von Lö sungsmitteln vorgenommen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 2,4-Dioxo- 3,3-di-n-propyl-5-brom- 6 -methyl-tetrahydro- pyridin, welches dadurch .gekennzeichnet ist, dass auf 2,4-Dioxo-3,3--di-n-propyl-6-methyl- tetrahydropyridin Brom einwirken gelassen wird.
Das neue 2,4-Dioxo-3,3-di-n-propyl-5- brom-6-methyl-tetrahydropyridin schmilzt bei 141-142' und ist in den gebräuchlichen organischen Lösungsmitteln leicht löslich. In wässerigen Alkalien löst sich die Verbindung unverändert mit gelblicher Farbe. Sie wirkt schlafmachend und soll als Arzneimittel ver wendet werden.
<I>Beispiel:</I> Unter Rühren löst man in 900 Volum- teilen Essigsäure von 80 % 209 Gewichtsteile 2,4-Dioxo - 3,3 -,di -n-propyl- 6 -methyl - tetra- hydropyridin. In die gekühlte Lösung tropft man bei etwa <B>10'</B> 160 Gewichtsteile Brom, gelöst in 300 Volumteilen Essigsäure von 80 %, ein.
Das 2,4-Dioxo-3,3-di-n-propyl-5- brom - 6 - methyl-tetrahydropyridin kristalli siert beim Verdünnen mit Wasser aus. FEs kann aus verdünntem Athylalkohol umgelöst werden und schmilzt bei 141-142'.
Process for the preparation of 2,4-diogo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine. It has been found that: by the action of halogenating agents on 2,4-dioxo-3,3-dialkyl-tetrahydropyrid-ine in a smooth reaction, the hydrogen in the 5-position can be substituted by halogen.
With the 1- or 6-methyl or. 1,6-dimethyl compounds, the reaction proceeds in the same direction and leads to similar compounds. The starting materials are obtained according to the process of Swiss Patent No. 187826 and its additives, as well as German Patents No. 637385 and 63 $ 532, It is surprising that in these conversions substitution takes place and not addition.
Nor can one see any behavior similar to that of pyridine, because the halogenations proceed quickly and smoothly under very mild conditions. These are therefore preferably carried out at low temperatures using solvents.
The subject of the present patent is a process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine, which is characterized in that on 2,4- Dioxo-3,3-di-n-propyl-6-methyl-tetrahydropyridine bromine is allowed to act.
The new 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine melts at 141-142 'and is easily soluble in common organic solvents. In aqueous alkalis, the compound dissolves unchanged with a yellowish color. It has a sleep-inducing effect and should be used as a medicine.
<I> Example: </I> While stirring, 209 parts by weight of 2,4-dioxo-3,3-, di-n-propyl-6-methyl-tetrahydropyridine are dissolved in 900 parts by volume of 80% acetic acid. 160 parts by weight of bromine, dissolved in 300 parts by volume of 80% acetic acid, are added dropwise to the cooled solution at about <B> 10 '</B>.
The 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine crystallizes out on dilution with water. FEs can be redissolved from dilute ethyl alcohol and melts at 141-142 '.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199680X | 1936-04-25 | ||
| CH193773T | 1937-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199680A true CH199680A (en) | 1938-08-31 |
Family
ID=25722579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199680D CH199680A (en) | 1936-04-25 | 1937-02-26 | Process for the preparation of 2,4-dioxo-3,3-di-n-propyl-5-bromo-6-methyl-tetrahydropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199680A (en) |
-
1937
- 1937-02-26 CH CH199680D patent/CH199680A/en unknown
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