CH296483A - Process for preparing 1-carbethoxy-4-n-butyryl-piperazine. - Google Patents
Process for preparing 1-carbethoxy-4-n-butyryl-piperazine.Info
- Publication number
- CH296483A CH296483A CH296483DA CH296483A CH 296483 A CH296483 A CH 296483A CH 296483D A CH296483D A CH 296483DA CH 296483 A CH296483 A CH 296483A
- Authority
- CH
- Switzerland
- Prior art keywords
- piperazine
- reaction
- butyryl
- carbethoxy
- preparing
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SLKWSZYSOUHYME-UHFFFAOYSA-N ethyl piperazine-1-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)N1CCNCC1 SLKWSZYSOUHYME-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Procédé de préparation de 1-carbéthoxy-4-n-butyryl-pipérazine. La présente invention se rapporte à un procédé de préparation de 1-carbéthoxy-4-n- but.y ryl-pipérazine de formule
EMI0001.0005
Selon l'invention, ce composé est préparé en faisant réagir de la 1-carbéthoxy-pipérazine avec un halogénure de n-butyryle.
Dans la. mise en aeuvre du présent procédé, on réalise la réaction, de préférence, dans un solvant anhydre tel que l'éther anhydre, l'acétate d'éthyle absolu, le benzène et analo gues. Dans certaines conditions, on peut réali ser la réaction dans un solvant. sensiblement aqueux en présence d'une substance alcaline qui joue le rôle d'accepteur pour l'hydracide halogéné libéré pendant la réaction.
On réalise, de préférence, la réaction à la température ambiante, bien qu'on puisse utili ser n'importe quelle température depuis -10 jusqu'à 100 C. Aux températures supérieures, la réaction est ordinairement achevée en -Lui temps allant de quelques minutes à quelques heures. Pour effectuer la réaction sous des ronclitions anhydres, on mélange par exemple les corps réagissants dans le solvant. à la teni- pérature ambiante, on laisse la réaction se produire à la, température ambiante, puis, éventuellement, on chauffe le mélange à une température allant jusqu'à 100 C.
Le composé préparé par le procédé selon l'invention présente un grand intérêt comme produit pharmaceutique nouveau, en raison de son activité physiologique et de sa toxicité relativement faible. <I>Exemple:</I> A une solution de 31,6 g (0,2 molécule) de1-carbéthoxy-pipérazine dans150 cm3 d'éther anhydre; on ajoute, en agitant, 21,3 g (20,7 em3; 0,2 molécule) de chlorure de n-butyryle. La. réaction se produit vigoureuse ment avec formation d'un précipité incolore de chlorhydrate de 1-carbéthoxy-pipérazine jusqu'au moment où la moitié du chlorure de n-butyryle a été ajoutée.
Après reflux pen dant 5 heures, on ajoute une solution de 31,6 g (0,2 molécule) de 1-carbéthoxy-pi- pérazine d'ans 25 em3 d'éther anhydre. On soumet le mélange réactionnel au reflux pen dant encore 3 heures. Après refroidissement, on filtre le mélange. On évapore l'éther du filtrat et on sépare par filtration le sirop d'une petite quantité de précipité. On distille le filtrat sous pression réduite. La 1-carb- éthoxy-4-n-butyryl-pipérazine distille sous forme d'un liquide incolore, de point d'ébulli tion 136-138 5 C sous 0,6 mm.
Le rendement est de 34,5 g (76% de la quantité théorique). Le produit., qui est soluble dans l'eau et les solvants organiques tels que l'éthanol, l'acé- tone, l'éther et le benzène, peut être hydro lysé en le faisant bouillir dans de l'acide ou de l'alcali aqueux.
Process for preparing 1-carbethoxy-4-n-butyryl-piperazine. The present invention relates to a process for the preparation of 1-carbethoxy-4-n-but.y ryl-piperazine of formula
EMI0001.0005
According to the invention, this compound is prepared by reacting 1-carbethoxy-piperazine with an n-butyryl halide.
In the. In carrying out the present process, the reaction is preferably carried out in an anhydrous solvent such as anhydrous ether, absolute ethyl acetate, benzene and the like. Under certain conditions, the reaction can be carried out in a solvent. substantially aqueous in the presence of an alkaline substance which acts as an acceptor for the halogenated hydracid released during the reaction.
The reaction is preferably carried out at room temperature, although any temperature can be used from -10 to 100 C. At higher temperatures, the reaction is usually completed in a few minutes. minutes to hours. In order to carry out the reaction under anhydrous conditions, the reactants are, for example, mixed in the solvent. at room temperature, the reaction is allowed to proceed at room temperature, then, optionally, the mixture is heated to a temperature of up to 100 ° C.
The compound prepared by the process according to the invention is of great interest as a new pharmaceutical product, on account of its physiological activity and its relatively low toxicity. <I> Example: </I> To a solution of 31.6 g (0.2 molecules) of 1-carbethoxy-piperazine in 150 cm3 of anhydrous ether; 21.3 g (20.7 em3; 0.2 molecules) of n-butyryl chloride are added with stirring. The reaction proceeds vigorously with the formation of a colorless precipitate of 1-carbethoxy-piperazine hydrochloride until half of the n-butyryl chloride has been added.
After refluxing for 5 hours, a solution of 31.6 g (0.2 molecules) of 1-carbethoxy-piperazine in 25 ml of anhydrous ether is added. The reaction mixture is refluxed for a further 3 hours. After cooling, the mixture is filtered. The ether is evaporated from the filtrate and the syrup is filtered off from a small amount of precipitate. The filtrate is distilled off under reduced pressure. The 1-carb-ethoxy-4-n-butyryl-piperazine distills off as a colorless liquid, boiling point 136-138 5 C at 0.6 mm.
The yield is 34.5 g (76% of the theoretical amount). The product, which is soluble in water and organic solvents such as ethanol, acetone, ether and benzene, can be hydrolyzed by boiling it in acid or l. aqueous alkali.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US296483XA | 1951-01-02 | 1951-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296483A true CH296483A (en) | 1954-02-15 |
Family
ID=21850145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296483D CH296483A (en) | 1951-01-02 | 1952-01-02 | Process for preparing 1-carbethoxy-4-n-butyryl-piperazine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296483A (en) |
-
1952
- 1952-01-02 CH CH296483D patent/CH296483A/en unknown
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