CH100407A - Process for the preparation of diethylaminoethylcarbamic acid phenylethyl ester. - Google Patents
Process for the preparation of diethylaminoethylcarbamic acid phenylethyl ester.Info
- Publication number
- CH100407A CH100407A CH100407DA CH100407A CH 100407 A CH100407 A CH 100407A CH 100407D A CH100407D A CH 100407DA CH 100407 A CH100407 A CH 100407A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethylaminoethylcarbamic
- water
- preparation
- acid
- phenylethyl ester
- Prior art date
Links
- NCWXNYLAYSHIRE-UHFFFAOYSA-N 2-phenylethyl n-[2-(diethylamino)ethyl]carbamate Chemical compound CCN(CC)CCNC(=O)OCCC1=CC=CC=C1 NCWXNYLAYSHIRE-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000009965 odorless effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 241000195493 Cryptophyta Species 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- -1 phenylethyl ester Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von Diätliylaminoäthylearbaminsäurephenyläthylester. Es wurde gefunden, dass man zum Diätliy laminoätliyl carbaminsäurephenyläthyl- ester gelangen kann, indem man auf Halogen- ameisensäui-ephenyläthy lester mindestens mo lekulare Mengen as-Diäthyläthylendiamin ein wirken lässt.
Die Reaktion kann sowohl in Wasser, als auch in indifferenten organischen Lösungs mitteln, wie z. B. Äther oder Benzol und der gleichen, bezw. in Gemischen von Wasser und organischen Lösungsmitteln, vorgenom men werden. Führt inan die Reaktion in Wasser aus, so kann man aus dem Re- aktionsprodukt auf Zusatz eines Alkalis, z. B. Natronlauge, die freie Base als<B>01</B> ab scheiden.
Zweckmässig verwendet man zur Reaktion auf 1 Mol. Halogenameisensäureester 2 Mol. as-Diäthyliithylendiamin, um die bei der Ein setzung entstehende Salzsäure zu binden. Statt des überschüssigen as-Diäthyläthylen- diamins können naturgemäss auch entspre chende Mengen von Alkalien, wie z. B. Natron lauge und dergleichen, verwendet werden. Der neue Körper- stellt in Form seiner freien Base ein in Wasser unlösliches, in den meisten organischen Lösungsmitteln lös liches, unter 0,025 nim Druck bei 147' sie dendes, farbloses, fast geruchloses ÖL dar.
Das Chlorhydrat ist in Wasser und gewissen organischen Lösungsmitteln, wie z. B. Alkohol und Aceton, löslich.
Die neue Verbindung soll zu therapeu tischen Zwecken verwendet werden. Beispiel 232 Teile as-Diäthyläthylendiamin wer den in 400 Teilen Eisund 100 Teilen Wasser gelöst. Nach einmaligem Zusatz von 184,5 Teilen Chlorameisensäurephenyläthylesterwird während einer Stunde gerührt. Hierauf wird durch Zusatz von Natronlauge die Base ab geschieden, in Äther aufgenommen und über Potasche getrocknet. Nach dem Verdunsten des Äthers wird sie im Vakuum destilliert.
Process for the preparation of phenylethyl diethylaminoethylearbamic acid. It has been found that diethylaminoethyl carbamic acid phenylethyl ester can be obtained by letting at least molecular amounts of as-diethylethylenediamine act on halogenated amine acid phenylethyl ester.
The reaction can mean both in water and in inert organic solvents, such as. B. ether or benzene and the like, respectively. in mixtures of water and organic solvents. If the reaction is carried out in water, the reaction product can be converted into an alkali, e.g. B. sodium hydroxide solution, which separates the free base as <B> 01 </B>.
It is expedient to use 2 mol of as-diethyliithylenediamine for the reaction to 1 mol of haloformic acid ester in order to bind the hydrochloric acid formed during the setting. Instead of the excess as-diethyläthylen- diamines can naturally also corresponding amounts of alkalis, such as. B. caustic soda and the like can be used. The new body, in the form of its free base, is a colorless, almost odorless oil that is insoluble in water, soluble in most organic solvents, under 0.025 mm under pressure at 147 '.
The chlorohydrate is in water and certain organic solvents, such as. B. alcohol and acetone, soluble.
The new compound is intended to be used for therapeutic purposes. Example 232 parts of as-diethylethylenediamine were dissolved in 400 parts of ice and 100 parts of water. After a single addition of 184.5 parts of phenylethyl chloroformate, the mixture is stirred for one hour. The base is then separated off by adding sodium hydroxide solution, taken up in ether and dried over potash. After the ether has evaporated, it is distilled in a vacuum.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH100407T | 1922-02-10 | ||
| CH99625T | 1922-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100407A true CH100407A (en) | 1923-08-01 |
Family
ID=25705622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100407D CH100407A (en) | 1922-02-10 | 1922-02-10 | Process for the preparation of diethylaminoethylcarbamic acid phenylethyl ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH100407A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721208A (en) * | 1951-11-30 | 1955-10-18 | Olin Mathieson | Quaternary-ammonium-salt of n-beta-aminoethyl carbamates |
-
1922
- 1922-02-10 CH CH100407D patent/CH100407A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721208A (en) * | 1951-11-30 | 1955-10-18 | Olin Mathieson | Quaternary-ammonium-salt of n-beta-aminoethyl carbamates |
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