CH243031A - Process for the preparation of an N-substituted imino-di-fatty acid amide. - Google Patents
Process for the preparation of an N-substituted imino-di-fatty acid amide.Info
- Publication number
- CH243031A CH243031A CH243031DA CH243031A CH 243031 A CH243031 A CH 243031A CH 243031D A CH243031D A CH 243031DA CH 243031 A CH243031 A CH 243031A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethylamide
- preparation
- butyl
- fatty acid
- butyric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 N- (n-butyl) - imino Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930007927 cymene Natural products 0.000 description 3
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PTECIXPBVVDNOU-UHFFFAOYSA-N molecular bromine;hydrate Chemical compound O.BrBr PTECIXPBVVDNOU-UHFFFAOYSA-N 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines N-substituierten Imino-di-fettsäureamides. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines N-substi- tuierten Imino-di-fettsäu.reamides. Das Ver fahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI0001.0006
und eine Verbindung der Formel
EMI0001.0007
worin X und Y reaktionsfähige, bei der Reaktion mit Ausnahme einer in ihnen ent haltenen
EMI0001.0008
sich abspaltende Reste bedeuten, zum N-(n- Butyl)
- imino - a - propionsäure-a'-buttersäure- bis-diäthylamid umsetzt. Die neue Verbindung soll als Arzneimit tel Verwendung finden. <I>Beispiel:</I> 42,8 Teile a-(n-Butylamino)-buttersäure- diäthylamid (dargestellt aus a-Brom-butter- säure-diäthylamid und n-Butylamin) werden in 100 Teilen Cymol gelöst und zum Sieden erhitzt.
Dazu tropft man bei 150 die Lö sung von 20,8 Teilen a-Brom-propionsäure- diäthylamid in & 0 Teilen Cymol und kocht die Mischung 10 Stunden weiter unter Rück fluss. Nach dem Erkalten wird das ausge schiedene Bromhydrat des a-(n-Butylamino)- buttersäure-diäthylamides durch Filtration entfernt.
Aus der Cymollösung wird das ge bildete N-(n-Butyl)-imino-a-propionsäure-a'- buttersäure-bis-diäthylamid durch Ausschüt- teln. mit Salzsäure isoliert, aus der salzsauren Lösung durch Sättigen mit Kaliumhydrogyd abgeschieden und in Xylol aufgenommen.
Nach dem Trocknen und Abdestillieren des Xylols wird das Produkt im FIochvakuum destilliert. Es ist ein fast farbloses, in Was- ser leicht lösliches 01 vom Siedepunkt 145 bis 148 unter 0,18 mm Druck. Mit organi schen Lösungsmitteln ist es mischbar und gibt mit Säuren lösliche Salze.
Zur gleichen Verbindung gelangt man durch Umsetzen von a-(n-Butylamino)-pro- pionsäure-diäthylamid mit a-Brom-butter- säure-diäthylamid.
Process for the preparation of an N-substituted imino-di-fatty acid amide. The subject of the present patent is a process for the production of an N-substituted imino-di-fatty acid reamide. The process is characterized in that a compound of the formula
EMI0001.0006
and a compound of the formula
EMI0001.0007
wherein X and Y are reactive, with the exception of one contained in them in the reaction
EMI0001.0008
residues which are split off mean to the N- (n-butyl)
- Imino - a - propionic acid-a'-butyric acid bis-diethylamide. The new compound is to be used as a drug. <I> Example: </I> 42.8 parts of a- (n-butylamino) -butyric acid diethylamide (prepared from a-bromo-butyric acid diethylamide and n-butylamine) are dissolved in 100 parts of cymene and brought to the boil heated.
The solution of 20.8 parts of a-bromopropionic acid diethylamide in 0 parts of cymene is added dropwise at 150 and the mixture is refluxed for a further 10 hours. After cooling, the separated bromine hydrate of a- (n-butylamino) - butyric acid diethylamide is removed by filtration.
The N- (n-butyl) -imino-a-propionic acid-a'-butyric acid-bis-diethylamide formed is extracted from the cymene solution by shaking. isolated with hydrochloric acid, deposited from the hydrochloric acid solution by saturation with potassium hydrogen and taken up in xylene.
After the xylene has been dried and distilled off, the product is distilled in a high vacuum. It is an almost colorless oil, easily soluble in water, with a boiling point of 145 to 148 under 0.18 mm pressure. It is miscible with organic solvents and produces soluble salts with acids.
The same compound is obtained by reacting a- (n-butylamino) propionic acid diethylamide with a-bromo-butyric acid diethylamide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243031T | 1943-05-13 | ||
| CH236876T | 1945-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243031A true CH243031A (en) | 1946-06-15 |
Family
ID=25728201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243031D CH243031A (en) | 1943-05-13 | 1943-05-13 | Process for the preparation of an N-substituted imino-di-fatty acid amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH243031A (en) |
-
1943
- 1943-05-13 CH CH243031D patent/CH243031A/en unknown
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