CH312687A - Process for the preparation of a basic substituted fatty acid amide - Google Patents
Process for the preparation of a basic substituted fatty acid amideInfo
- Publication number
- CH312687A CH312687A CH312687DA CH312687A CH 312687 A CH312687 A CH 312687A CH 312687D A CH312687D A CH 312687DA CH 312687 A CH312687 A CH 312687A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- fatty acid
- acid amide
- substituted fatty
- basic substituted
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 4
- 239000000194 fatty acid Substances 0.000 title claims description 4
- 229930195729 fatty acid Natural products 0.000 title claims description 4
- 150000004665 fatty acids Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 5
- 239000012230 colorless oil Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002904 solvent Substances 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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 Herstellung eines basisch substituierten Fettsäureamides Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, wel ches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI0001.0004
mit Diäthylamin umsetzt. Die Umsetzung kann in An- oder Abwesenheit von Lösungs- bzw. Verdünnungsmitteln und Anlagerungs- katalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des Diäthylamins unter Druck gearbeitet.
Als Anlagerungs- katalysatoren benützt man vorteilhaft quater- nä.re Ammoniumbasen, wie z. B. Trimethyl- benzylammoniumhydroxyd.
Das so erhaltene ss-Diäthylamino-propion- säure-N-(3-phenoxy-propyl-2)-äthylamid ist ein farbloses, unter 0,01 mm bei 150-151 siedendes Öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden.
<I>Beispiel</I> Ein Gemisch von 16,0 g Acrylsäure-N-(3- plienoxy-propyl-2)-äthylamid, 17,0 g Diäthyl- amin und einigen Tropfen Trimethyl-benzyl- ammoniumhydroxyd wird im Autoklaven wäh rend einigen Stunden auf 145 erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rückstand in Äther aufgenommen und mit 2n-Salzsäure ausgezogen.
Der salzsaure Aus zug wird gut mit Äther gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein Öl ausscheidet, welches in Äther aufgenom men wird. Nach dem Trocknen über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert. Man gewinnt so das ,B-Diäthylamino-propionsäure-N- (3- phenoxy-propyl-2)-äthylamid als farbloses Öl, welches unter 0,01 mm bei 150-151 siedet..
Process for the preparation of a basic substituted fatty acid amide The subject of the present patent forms a process for the preparation of a new basic substituted fatty acid amide, which is characterized in that a compound of the formula
EMI0001.0004
Reacts with diethylamine. The reaction can take place in the presence or absence of solvents or diluents and addition catalysts. Because of the volatility of the diethylamine, it is preferable to work under pressure.
The addition catalysts used are advantageously quaternary ammonium bases, such as B. trimethylbenzylammonium hydroxide.
The β-diethylamino-propionic acid-N- (3-phenoxy-propyl-2) -ethylamide obtained in this way is a colorless oil boiling below 0.01 mm at 150-151.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.
<I> Example </I> A mixture of 16.0 g of acrylic acid-N- (3-plienoxy-propyl-2) -ethylamide, 17.0 g of diethylamine and a few drops of trimethylbenzylammonium hydroxide is mixed in the autoclave heated to 145 for a few hours. The excess diethylamine is distilled off, the residue is taken up in ether and extracted with 2N hydrochloric acid.
The hydrochloric acid extract is washed well with ether and then alkalized with concentrated lye, an oil separating out, which is taken up in ether. After drying over potash, the ether is evaporated and the residue is distilled in a high vacuum. The B-diethylamino-propionic acid-N- (3-phenoxy-propyl-2) -ethylamide is thus obtained as a colorless oil which boils at 150-151 below 0.01 mm.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312687T | 1952-06-08 | ||
| CH306512T | 1952-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH312687A true CH312687A (en) | 1956-02-15 |
Family
ID=25735185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH312687D CH312687A (en) | 1952-06-08 | 1952-06-08 | Process for the preparation of a basic substituted fatty acid amide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH312687A (en) |
-
1952
- 1952-06-08 CH CH312687D patent/CH312687A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH312689A (en) | Process for the preparation of a basic substituted fatty acid amide | |
| CH312688A (en) | Process for the preparation of a basic substituted fatty acid amide | |
| CH312690A (en) | Process for the preparation of a basic substituted fatty acid amide | |
| CH311687A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311581A (en) | Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). | |
| CH328669A (en) | Process for the production of a new basic substituted fatty acid amide | |
| CH311669A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311684A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311671A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311697A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311693A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311658A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311679A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311661A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311665A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311692A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311647A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311694A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311683A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311663A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311705A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311686A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH311649A (en) | Process for the production of a new basic substituted fatty acid amide. | |
| CH185280A (en) | Process for the preparation of the diethylamide of 3,5-dimethylisoxazole-4-carboxylic acid. | |
| CH311667A (en) | Process for the production of a new basic substituted fatty acid amide. |