CH240401A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH240401A CH240401A CH240401DA CH240401A CH 240401 A CH240401 A CH 240401A CH 240401D A CH240401D A CH 240401DA CH 240401 A CH240401 A CH 240401A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- preparation
- aliphatic
- aminocarboxamide
- acid dimethylamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 3
- 125000001931 aliphatic group Chemical group 0.000 title claims description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic amino acid Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines acylierten, aliphatischen Aminoearbonsäureamids. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbon- säureamids. Das Verfahren ist dadurch ge kennzeichnet, dass ein a-Halogen-iso-valerian- säuredimethylamid mit n-Propylamin umge setzt und das Reaktionsprodukt acetyliert wird.
Das N-Acetyl-a-(n-propylamino)-iso- valeriansäuredimethylamid der Formel
EMI0001.0014
bildet eine farblose Flüssigkeit vom Siede punkt T15-117 unter 0,2 mm.
Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> 37,2 Teile a-(n-Propylamino)-iso-valerian- säuredimethylamid, Kp, 110-113 (darge stellt aus a-Brom-iso-valeriansäuredimethyl- amid durch Erhitzen mit n-Propylamin), werden in 200 Teilen Benzol gelöst und unter Rühren und Kühlen 20,4 Teile Essigsäure anhydrid zugetropft. Man erwärmt 1 Stunde zum Sieden. Nach dem Abkühlen gibt man Wasser zu, sättigt mit galiumhydrogyd und trennt die Benzollösung ab.
Nach dem Ab destillieren des Lösungsmittels wird das Re aktionsprodukt im Hochvakuum rektifiziert. Die neue Verbindung siedet bei 115-117 unter 0,2 mm und ist löslich' in Wasser und organischen Lösungsmitteln.
Process for the preparation of an acylated, aliphatic amino acid amide. The subject of the present additional patent is a process for the preparation of an acylated, aliphatic aminocarboxylic acid amide. The process is characterized in that an α-halo-valeric acid dimethylamide is reacted with n-propylamine and the reaction product is acetylated.
The N-acetyl-a- (n-propylamino) -isovaleric acid dimethylamide of the formula
EMI0001.0014
forms a colorless liquid with a boiling point T15-117 below 0.2 mm.
The new compound should find therapeutic use.
<I> Example: </I> 37.2 parts of a- (n-propylamino) -iso-valeric acid dimethylamide, bp, 110-113 (shown is made from a-bromo-iso-valeric acid dimethyl amide by heating with n- Propylamine) are dissolved in 200 parts of benzene, and 20.4 parts of acetic anhydride are added dropwise with stirring and cooling. The mixture is heated to the boil for 1 hour. After cooling, water is added, saturated with galium hydrogen and the benzene solution is separated off.
After the solvent has been distilled off, the reaction product is rectified in a high vacuum. The new compound boils below 0.2 mm at 115-117 and is soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234453T | 1942-12-18 | ||
| CH240401T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240401A true CH240401A (en) | 1945-12-15 |
Family
ID=25727918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240401D CH240401A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240401A (en) |
-
1942
- 1942-12-18 CH CH240401D patent/CH240401A/en unknown
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