CH199678A - Process for the preparation of 1-methyl-2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine. - Google Patents
Process for the preparation of 1-methyl-2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine.Info
- Publication number
- CH199678A CH199678A CH199678DA CH199678A CH 199678 A CH199678 A CH 199678A CH 199678D A CH199678D A CH 199678DA CH 199678 A CH199678 A CH 199678A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethyl
- methyl
- dioxo
- bromo
- tetrahydropyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- PETRHGPKIZDGTL-UHFFFAOYSA-N 5-bromo-3,3-diethyl-1-methylpiperidine-2,4-dione Chemical compound CN1C(C(C(C(C1)Br)=O)(CC)CC)=O PETRHGPKIZDGTL-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
- 239000003814 drug Substances 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DBUNKXKRXZUZLR-UHFFFAOYSA-N 4,4-diethyl-2,3-dihydro-1H-pyridine Chemical compound C(C)C1(CCNC=C1)CC DBUNKXKRXZUZLR-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
- 239000003795 chemical substances by application 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 group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003960 organic solvent 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 1-llethyl-2,4-dioao-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 substi- tuiert 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.6,37385 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 1-Methyl- 2,4-diogo-3;3"diäthyl- 5 -brom-tetrahydropyri- din, welches daJurch gekennzeichnet ist, dass auf 1- Methyl - 2,4 - diogo-3,3-diäthyl-tetra- hydropyridin Brom einwirken gelassen wird.
Das neue 1-Methyl-2,4-diogo-3,3@-diäthyl- 5-brom-tetrahydropyridin schmilzt bei 80 bis <B>81'</B> und ist in den gebräuchlichen organi schen Lösungsmitteln leicht löslich. In wäs serigen Alkalien löst sich die Verbindung unverändert mit gelblicher Farbe. Sie wirkt schlafmachend und soll als Arzneimittel ver wendet werden.
<I>Beispiel:</I> Zu einer Lösung von 181 Gewichtsteilen 1-Methyl- 2,4-,diogo- 3,.3-,diäthyl-tetrahydro- pyridin in 600 Volumteilen Chloroform lässt man unter Rühren bei etwa -E- <B>10'</B> eine Lö sung von 160 Gewichtsteilen Brom in 300 Volumenteilen Chloroform eintropfen. Das Brom verschwindet sofort und Bromwasser- Stoff entweicht. Nach dem Abdunsten des Chloroforms hinterbleibt
1-Methyl-2,4-diogo- 3,3-diäthyl-5-brom-tetrahydropyridin in fe ster Form. Es kann aus der ungefähr glei chen Gewiehtsmenge Dibutyläther umgelöet erden.
Process for the preparation of 1-llethyl-2,4-dioao-3,3-diethyl-5-bromo-tetrahydropyridine. It has been found that the action of halogenating agents on 2,4-diogo-3,3-dialkyl-tetrahydropyridines in a smooth reaction of the hydrogen in the 5-position can be substituted by halogen.
With the 1- or 6-methyl- respectively. 1,6-dimethyl compounds - the implementation is quite the same and leads to similar compounds. The starting materials are obtained according to the process of Swiss patent No. 187826 and its additives, and German patents No. 6,37385 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 1-methyl-2,4-diogo-3; 3 "diethyl-5-bromo-tetrahydropyridine, which is characterized by the fact that 1-methyl-2,4-diogo -3,3-diethyl-tetrahydropyridine bromine is allowed to act.
The new 1-methyl-2,4-diogo-3,3 @ -diethyl-5-bromo-tetrahydropyridine melts at 80 to 81 '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 is intended to be used as a medicine.
<I> Example: </I> To a solution of 181 parts by weight of 1-methyl-2,4-, diogo- 3, .3-, diethyl-tetrahydropyridine in 600 parts by volume of chloroform is allowed with stirring at about -E- <B> 10 '</B> drop in a solution of 160 parts by weight of bromine in 300 parts by volume of chloroform. The bromine disappears immediately and hydrogen bromine substance escapes. Remains after the chloroform has evaporated
1-Methyl-2,4-diogo- 3,3-diethyl-5-bromo-tetrahydropyridine in solid form. Dibutyl ether can be redissolved from approximately the same weight.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199678X | 1936-04-25 | ||
| CH193773T | 1937-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199678A true CH199678A (en) | 1938-08-31 |
Family
ID=25722577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199678D CH199678A (en) | 1936-04-25 | 1937-02-26 | Process for the preparation of 1-methyl-2,4-dioxo-3,3-diethyl-5-bromo-tetrahydropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199678A (en) |
-
1937
- 1937-02-26 CH CH199678D patent/CH199678A/en unknown
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