CH272504A - Process for preparing 1-piperazine-N, N-diethylcarboxamide. - Google Patents
Process for preparing 1-piperazine-N, N-diethylcarboxamide.Info
- Publication number
- CH272504A CH272504A CH272504DA CH272504A CH 272504 A CH272504 A CH 272504A CH 272504D A CH272504D A CH 272504DA CH 272504 A CH272504 A CH 272504A
- Authority
- CH
- Switzerland
- Prior art keywords
- piperazine
- reaction
- carried out
- chloroform
- water
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000009738 saturating Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Procédé de préparation de 1-pipérazine-N,N-diéthylcarboxamide. l@a présente invention se rapporte à un procédé de préparation d'un monocarboxamide de pipérazine, le 1-pipérazine-N,N-diéthyl- carboxamide, qui est un composé nouveau de formule:
EMI0001.0008
Suivant l'invention, on prépare ce com posé en faisant réagir de la pipérazine avec du chlorure de diéthyl-carbamyle. La réaction est effectuée avantageusement à une tempé rature comprise entre 0 et 400 C, de préfé rence à la température ambiante, dans un solvant, par exemple le chloroforme, le tétra chlorure (le carbone, l'aeétate éthylique ou ].'eau.
lie 1-pipérazine-N,N-diéthyl-carboxamide obtenu par le procédé suivant la présente in vention est une substance incolore à. jaune pâle, soluble dans le chloroforme, l'éther, l'acétone, l'éthanol et l'eau. Les sels d'acides de cet amide sont des solides blancs solubles dans l'eau.
Lorsque le chloroforme ou un solvant or ganique similaire est utilisé pour la mise en aeuvre (lu procédé selon l'invention, il est pré férable de récupérer le produit en saturant d'abord le mélange réactionnel par de l'acidé chlorhydrique gazeux, à basse température. La pipérazine n'ayant par réagi précipite sous forme de son chlorhydrate, que l'on peut éliminer par filtrage.
On concentre le mélange réactionnel en chassant. le solvant et on traite le chlorhydrate de 1-pipérazine-N,N-diéthyl- carboxamide qui se sépare sous forme solide, pour en régénérer la base, éventuellement après recristallisation.
Lorsque la réaction est effectuée dans de l'eau comme solvant (de préférence addition née d'un alcali), le mode préféré de récupé ration du produit consiste à saturer le mé lange réactionnel par du carbonate de potas sium, du sulfate d'ammonium ou un sel ana logue. On extrait ensuite le produit au moyen d'un solvant, par exemple d'éther ou de chloro forme, de préférence sous forme anhydre, et ensuite on distille l'extrait.
Le 1-pipérazine-N,N-.diéthyl-carboxamide peut être utilisé dans le traitement. de la filiarose et comme sédatif.
Une mise en aeuvre du procédé de la pré sente invention est exposée dans l'exemple suivant.
Exemple: On prépare une solution de 32 g de pipér- azine anhydre dans 225 cm@ d'alcool éthylique et on y ajoute 50 g de chlorure de diéthyl carbamyle par petites portions. Lorsque la quantité entière a, été ajoutée, un solide com- menee à se séparer. On ajoute alors environ 7.00 cm- d'eau pour dissoudre ce solide.
On laisse reposer le mélange pendant 24 heures après quoi on l'évapore dans le vide pour ob- tenir un volume d'environ 75 cm#. Le mélange est épuisé au moyen d'éther, l'extrait éthéré étant ensuite séché >sur du sulfate de magné sium et distillé. On obtient un rendement de 21,7 g de 1-pipér azine-N,N-diéthyl-,carboxamide qui est une substance liquide incolore à jaune pâle, soluble dans le chloroforme, l'éther, l'acétone, l'éthanol et l'eau et formant facile ment des sels. Son poids moléculaire est de 185 et son point d'ébullition est de 1340 C/6 mm.
Process for preparing 1-piperazine-N, N-diethylcarboxamide. The present invention relates to a process for preparing a piperazine monocarboxamide, 1-piperazine-N, N-diethylcarboxamide, which is a novel compound of formula:
EMI0001.0008
According to the invention, this compound is prepared by reacting piperazine with diethylcarbamyl chloride. The reaction is advantageously carried out at a temperature between 0 and 400 ° C., preferably at room temperature, in a solvent, for example chloroform, tetrachloride (carbon, ethyl acetate or] water.
1-piperazine-N, N-diethyl-carboxamide obtained by the process according to the present invention is a colorless substance to. pale yellow, soluble in chloroform, ether, acetone, ethanol and water. The acid salts of this amide are white solids soluble in water.
When chloroform or a similar organic solvent is used for the implementation (the process according to the invention, it is preferable to recover the product by first saturating the reaction mixture with gaseous hydrochloric acid, at low Temperature Unreacted piperazine precipitates as its hydrochloride, which can be filtered off.
The reaction mixture is concentrated while driving off. the solvent and treating the hydrochloride of 1-piperazine-N, N-diethylcarboxamide which separates in solid form, to regenerate the base, optionally after recrystallization.
When the reaction is carried out in water as a solvent (preferably the addition of an alkali), the preferred method of recovering the product consists in saturating the reaction mixture with potassium carbonate, ammonium sulphate. or an analogous salt. The product is then extracted with a solvent, for example ether or chloroform, preferably in anhydrous form, and the extract is then distilled.
1-Piperazine-N, N-.diethyl-carboxamide can be used in the treatment. filiarosis and as a sedative.
An implementation of the process of the present invention is set out in the following example.
Example: A solution of 32 g of anhydrous piperazine in 225 cc of ethyl alcohol is prepared and 50 g of diethyl carbamyl chloride are added thereto in small portions. When the entire amount has been added a solid begins to separate. About 7.00 cm 3 of water are then added to dissolve this solid.
The mixture is allowed to stand for 24 hours after which it is evaporated in vacuo to obtain a volume of about 75 cm 3. The mixture is stripped with ether, the ethereal extract then being dried over magnesium sulfate and distilled. A yield of 21.7 g of 1-piper azine-N, N-diethyl-, carboxamide is obtained which is a colorless to pale yellow liquid substance, soluble in chloroform, ether, acetone, ethanol and water and easily forming salts. Its molecular weight is 185 and its boiling point is 1340 C / 6 mm.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US272504XA | 1946-04-12 | 1946-04-12 | |
| CH268051T | 1947-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH272504A true CH272504A (en) | 1950-12-15 |
Family
ID=25730982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH272504D CH272504A (en) | 1946-04-12 | 1947-04-10 | Process for preparing 1-piperazine-N, N-diethylcarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH272504A (en) |
-
1947
- 1947-04-10 CH CH272504D patent/CH272504A/en unknown
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