CH257637A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH257637A CH257637A CH257637DA CH257637A CH 257637 A CH257637 A CH 257637A CH 257637D A CH257637D A CH 257637DA CH 257637 A CH257637 A CH 257637A
- Authority
- CH
- Switzerland
- Prior art keywords
- propylamino
- propionyl
- butyric acid
- parts
- dimethylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 125000001931 aliphatic group Chemical group 0.000 title claims description 4
- 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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PYDAOFFTNGHDLV-UHFFFAOYSA-N ClO.C(CC)N Chemical compound ClO.C(CC)N PYDAOFFTNGHDLV-UHFFFAOYSA-N 0.000 description 1
- FMSSTWGVVMAWCY-UHFFFAOYSA-N ClO.CNC Chemical compound ClO.CNC FMSSTWGVVMAWCY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-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, aliphatisehen Aminocarbonsäureamids. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Darstellung @@irics acylierten, aliphatischen Aminoca.rbon- #äureamid5. Das Verfahren ist dadurch ge kennzeichnet, dass man eine den N-Propionyl- (c-(n-propylamino)-n-buttersä.urerest abge- i,
ende Verbindung mit Dimethylamin um setzt.
Das N-Propionyl-a-(n-propylamino)-n- i@ut.tersäuredimethylamid der Formel
EMI0001.0019
bildet: eine farblose. Flüssigkeit vom Siede punkt 119-120 C unter 0,2 mm. Die neue Verbindung soll therapeutische Verwendung finden.
Betspiel <I>1:</I> 72,5 Teile a-(n-Propylamino)-n-butter- säirre werden in 250 Teilen Chloroform ge löst und unter Rühren und Kühlen 23,5 Teile Propion;
vlchlorid zugetropft. Nach zweistün- digem Rühren wird vom a-(n-Propylamino)- ri.-liuttersäure-ehlorhydra.t abfiltriert, die Chloroformlösung mit 52 Teilen Phosphor <B>1</B> !eritaehlorid versetzt und einige Zeit bei Zim- in(,rtemperatrrr gerührt. Zur Beendigung der Reaktion wird noch kurze Zeit zum Sieden erhitzt.
Nach dem Abdestillieren von Chloro form und Pliophoroxyclllorid wird das rohe Säurechlorid unter Kühlung zu einer äthe- risehen Dimethy laminlösung gegeben. Nach :1lifilti-ieren vorn Dimethyla.minchlorhydrat wird die ätherische Lösung mit gesättigter Kalilauge durchgeschüttelt und abgetrennt. Das Lösungsmittel wird abdestilliert und der Rückstand im Hochvakuum rektifiziert.
Die neue Verbindung zeigt den Siedepunkt 119 bis 120 C unter 0,2 mm, und ist leicht löslich in Wasser und in organischen Lösungsmitteln. <I>Beispiel 2:</I> 195 Teile a-Brom-n-buttersäureäthylester werden mit 150 Teilen n-Propylamin und 300 Teilen Benzol im Autoklaven 6 Stunden auf 80 C erwärmt.
Vom n-Propylamin-chlor- hydrat wird filtriert, das Benzol abdestlliert und der Rückstand im Vakuum rektifiziert, Kp20 90-92 C. 86,5 Teile des. a-(n-Propyl- amino)-n-buttersäureäthyl@esters werden in ?00 Teilen Äther gelöst und unter Rühren und Kühlen 23.5 Teile Propionylchlorid zu getropft.
Nach zweistündigem Rühren wird vom a-(n-Propylamino)-n-buttersäureäthyl- ester-chlorhydrat abfiltriert und das Lö sungsmittel abdestilliert. Das Reaktionspro dukt wird im Autoklaven mit 45 Teilen Di- rrrethyla.min in 150 Teilen Benzol auf 160 bis 180 C erhitzt, wobei das N-Propionyl-a- (n-propylamino) -n-buttersäuredimethylamid vom Siedepunkt 119-120 C unter 0,2 mm entsteht.
Die neue Verbindung ist leicht lös lich in Wasser und organischen. Lösungs- mitteln.
Zu der gleichen Verbindung kann. man auch durch Verseifen des a-(n-Propylamino)- \T- propionyl - n-buttersäureäthylesters, Über- führen -der Säure in das entsprechende Halo genid und Behandeln mit Dimethylamin, ge langen.
Process for the preparation of an acylated, aliphatic aminocarboxamide. The subject of the present additional patent is a process for the preparation of @@ irics acylated, aliphatic Aminoca.rbon- # äureamid5. The process is characterized in that one of the N-propionyl- (c- (n-propylamino) -n-butyric acid residue is removed i,
End connection with dimethylamine sets.
The N-propionyl-a- (n-propylamino) -n- i@ut.tersäuredimethylamid of the formula
EMI0001.0019
forms: a colorless one. Liquid with a boiling point of 119-120 C below 0.2 mm. The new compound should find therapeutic use.
Betspiel <I> 1: </I> 72.5 parts of a- (n-propylamino) -n-butyric acid are dissolved in 250 parts of chloroform and, with stirring and cooling, 23.5 parts of propion;
vlchlorid added dropwise. After two hours of stirring, the a- (n-propylamino) - ri.-liutyric acid ehlorhydra.t is filtered off, the chloroform solution is mixed with 52 parts of phosphorus, and for some time at Zim- in ( The mixture is heated to boiling for a short time to complete the reaction.
After the chloroform and pliophoroxy chloride have been distilled off, the crude acid chloride is added to an ethereal dimethylamine solution with cooling. After: 1lifilti-ation from the dimethylamine chlorohydrate, the ethereal solution is shaken through with saturated potassium hydroxide solution and separated. The solvent is distilled off and the residue is rectified in a high vacuum.
The new compound has a boiling point of 119 to 120 C below 0.2 mm, and is easily soluble in water and in organic solvents. Example 2 195 parts of a-bromo-n-butyric acid ethyl ester are heated to 80 ° C. for 6 hours in an autoclave with 150 parts of n-propylamine and 300 parts of benzene.
The n-propylamine chlorohydrate is filtered off, the benzene is distilled off and the residue is rectified in vacuo, boiling point 90-92 ° C. 86.5 parts of the a- (n-propylamino) -n-butyric acid ethyl ester are dissolved in ? 00 parts of ether are dissolved and 23.5 parts of propionyl chloride are added dropwise with stirring and cooling.
After two hours of stirring, the a- (n-propylamino) -n-butyric acid ethyl ester chlorohydrate is filtered off and the solvent is distilled off. The reaction product is heated in an autoclave with 45 parts of di- rrrethyla.min in 150 parts of benzene to 160 to 180 ° C., the N-propionyl-a- (n-propylamino) -n-butyric acid dimethylamide with a boiling point of 119-120 ° C. below 0 , 2 mm arises.
The new compound is easily soluble in water and organic. Solvents.
To the same connection can. can also be achieved by saponifying the a- (n-propylamino) - \ T-propionyl-n-butyric acid ethyl ester, converting the acid into the corresponding halide and treating with dimethylamine.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH251249T | 1942-12-18 | ||
| CH257637T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257637A true CH257637A (en) | 1948-10-15 |
Family
ID=25729522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257637D CH257637A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257637A (en) |
-
1942
- 1942-12-18 CH CH257637D patent/CH257637A/en unknown
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