CH253184A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253184A CH253184A CH253184DA CH253184A CH 253184 A CH253184 A CH 253184A CH 253184D A CH253184D A CH 253184DA CH 253184 A CH253184 A CH 253184A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- preparation
- aliphatic
- aminocarboxamide
- propylamino
- Prior art date
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WBGWGHYJIFOATF-UHFFFAOYSA-M potassium;methyl sulfate Chemical compound [K+].COS([O-])(=O)=O WBGWGHYJIFOATF-UHFFFAOYSA-M 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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 Aminocarbonsäureamii#\s7 Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäure- amids. Das Verfahren ist dadurch gekenn zeichnet, dass N-Acetyl-a-(n-propylamino)-n- buttersäureamid am Amidstickstoff bis zum Ersatz beider Wasserstoffatome methyliert wird.
Das N-Acetyl-a-(n-propylamino)-n-butter- säuredimethylamid der Formel
EMI0001.0014
bildet eine farblose Flüssigkeit vom Siede punkt 129 unter 0,31 mm.
Die neue Verbindung soll therapeutische Verwendung finden. Beispiel: 26- Teile a-(n-Propylamino)-n-buttersäure- amid werden in Chloroform gelöst und bei t) mit 7,8 Teilen Acetylchlorid zur Reak tion gebracht. Vom a-(n-Propylamino)-n-but- tersäureamid-chlorhydrat wird filtriert und das Chloroform abdestilliert. Der Rückstand wird in 200 Teilen Xylol aufgenommen und mit 10 Teilen Natriumamid eine. Stunde zum Sieden erhitzt.
Nach dem Abkühlen werden 38 Teile Kalium-methylsulfat zugegeben und anschliessend wird im Druckgefäss auf 180 bis 190 erhitzt. Nach beendeter Reaktion wie derholt man die Behandlung mit Natrium- amid und Kalium-methylsulfat. Dann giesst man auf Eis, sättigt die wä.ssrige Lösung mit festem Kaliumhydrogyd und trennt die Xylollösung ab. Das Lösungsmittel wird ab destilliert und der Rückstand im Hochvakuum rektifiziert. Die neue Verbindung zeigt den Siedepunkt 129 unter 0,31 mm und ist leicht löslich in Wasser und organischen Lösungs mitteln. .
Process for the preparation of an acylated, aliphatic aminocarboxylic acid amide The subject of the present additional patent is a process for the preparation of an acylated, aliphatic aminocarboxamide. The process is characterized in that N-acetyl-a- (n-propylamino) -n-butyric acid amide is methylated on the amide nitrogen until both hydrogen atoms are replaced.
The N-acetyl-a- (n-propylamino) -n-butyric acid dimethylamide of the formula
EMI0001.0014
forms a colorless liquid with a boiling point of 129 below 0.31 mm.
The new compound should find therapeutic use. Example: 26 parts of a- (n-propylamino) -n-butyric acid amide are dissolved in chloroform and reacted with 7.8 parts of acetyl chloride at t). The a- (n-propylamino) -n-but-acid amide chlorohydrate is filtered off and the chloroform is distilled off. The residue is taken up in 200 parts of xylene and treated with 10 parts of sodium amide. Heated to the boil for an hour.
After cooling, 38 parts of potassium methyl sulfate are added and the mixture is then heated to 180 to 190 in a pressure vessel. After the reaction has ended, the treatment with sodium amide and potassium methyl sulfate is repeated. Then it is poured onto ice, the aqueous solution is saturated with solid potassium hydrogen and the xylene solution is separated off. The solvent is distilled off and the residue is rectified in a high vacuum. The new compound has a boiling point of 129 below 0.31 mm and is easily soluble in water and organic solvents. .
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253184T | 1942-12-18 | ||
| CH244952T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253184A true CH253184A (en) | 1948-02-15 |
Family
ID=25729010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253184D CH253184A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253184A (en) |
-
1942
- 1942-12-18 CH CH253184D patent/CH253184A/en unknown
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