AT206891B - Process for the preparation of new tertiary amines - Google Patents
Process for the preparation of new tertiary aminesInfo
- Publication number
- AT206891B AT206891B AT801158A AT801158A AT206891B AT 206891 B AT206891 B AT 206891B AT 801158 A AT801158 A AT 801158A AT 801158 A AT801158 A AT 801158A AT 206891 B AT206891 B AT 206891B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- tertiary amines
- general formula
- new tertiary
- alkyl
- Prior art date
Links
- 150000003512 tertiary amines Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- VXGQDFOHLMAZIV-UHFFFAOYSA-N 1-phenylpentan-2-amine Chemical compound CCCC(N)CC1=CC=CC=C1 VXGQDFOHLMAZIV-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 benzylmagnesium halides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen tertiären Aminen
In der österr. Patentschrift Nr. 203496 ist ein Verfahren zur Herstellung von neuen terti- ären Aminen der allgemeinen Formel :
EMI1.1
beschrieben, wobei Nitrile der allgemeinen Formel :
EMI1.2
mit Benzylmagnesiumhalogeniden in Gegenwart von Lösungsmitteln umgesetzt und die erhaltenen Reaktionsprodukte gegebenenfalls quaternisiert werden.
In diesen Formeln bedeuten R Wasserstoff, eine Alkyl- oder Alkoxygruppe und Z einen gerad- oder verzweigtkettigen Alkyl-oder Alkenylrest.
Es wurde nun gefunden, dass man tertiäre Amine der allgemeinen Formel :
EMI1.3
worin R Wasserstoff, eine Alkyl- oder Alkoxygruppe und A einen gerad- oder verzweigtkettigen Alkyl- oder Alkenylrest mit mindestens 2 Kohlenstoffatomen bedeuten, in guter Ausbeute erhält, wenn man auf primäre Amine der allgemeinen Formel :
EMI1.4
worin R und A die oben angegebene Bedeutung zukommt, in an sich bekannter Weise 1, 4-Dihalogenbutan einwirken lässt, wobei der Pyrrolidinring gebildet wird.
Die erfindungsgemäss erhaltenen Verbindungen sind wertvolle Therapeutika. Die Wirkungen wurden bereits in der österr. Patentschrift Nr.
203496 abgehandelt.
Beispiel : 7 g l-Phenyl-2-amino-pentan und 9 g 1, 4-Dibrombutan werden mit 2 g Natriumacetat in 50 cm3 Isopropanol 4 Stunden unter Rückfluss erhitzt. Nach dem Abdestillieren des Isopropanols nimmt man den Rückstand in verdünnter Salzsäure auf und wäscht ihn mit Äther.
Die saure wässerige Schicht wird dann alkalisch gemacht und das abgeschiedene Öl in Äther aufgenommen, das nach dem Trocknen über Natriumsulfat und Verjagen des Lösungsmittels destilliert wird. Man erhält 4 g l-Phenyl-2- pyrrolidino-pentan vom Kpo, ? ;, = 1000 C, dessen aus Aceton umkristallisiertes Hydrochlorid bei 133-1348 C schmilzt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of new tertiary amines
In the Austrian patent specification no. 203496 there is a process for the preparation of new tertiary amines of the general formula:
EMI1.1
described, where nitriles of the general formula:
EMI1.2
reacted with benzylmagnesium halides in the presence of solvents and the reaction products obtained are optionally quaternized.
In these formulas, R is hydrogen, an alkyl or alkoxy group, and Z is a straight or branched alkyl or alkenyl radical.
It has now been found that tertiary amines of the general formula:
EMI1.3
where R is hydrogen, an alkyl or alkoxy group and A is a straight or branched chain alkyl or alkenyl radical with at least 2 carbon atoms, is obtained in good yield if one uses primary amines of the general formula:
EMI1.4
in which R and A have the meaning given above, in a manner known per se, 1,4-dihalobutane is allowed to act, the pyrrolidine ring being formed.
The compounds obtained according to the invention are valuable therapeutic agents. The effects were already mentioned in the Austrian patent no.
203496 dealt with.
Example: 7 g of 1-phenyl-2-aminopentane and 9 g of 1,4-dibromobutane are refluxed with 2 g of sodium acetate in 50 cm3 of isopropanol for 4 hours. After the isopropanol has been distilled off, the residue is taken up in dilute hydrochloric acid and washed with ether.
The acidic aqueous layer is then made alkaline and the separated oil taken up in ether which, after drying over sodium sulfate and driving off the solvent, is distilled. 4 g of l-phenyl-2-pyrrolidino-pentane from the Kpo are obtained, ;, = 1000 C, whose hydrochloride recrystallized from acetone melts at 133-1348 C.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE206891X | 1957-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT206891B true AT206891B (en) | 1959-12-28 |
Family
ID=5793407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT801158A AT206891B (en) | 1957-05-27 | 1958-05-08 | Process for the preparation of new tertiary amines |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT206891B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1161274B (en) * | 1960-04-07 | 1964-01-16 | Thomae Gmbh Dr K | Process for the preparation of ª ‡ -Pyrrolidinoketonen and their salts |
-
1958
- 1958-05-08 AT AT801158A patent/AT206891B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1161274B (en) * | 1960-04-07 | 1964-01-16 | Thomae Gmbh Dr K | Process for the preparation of ª ‡ -Pyrrolidinoketonen and their salts |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH409980A (en) | Process for the preparation of substituted 2-arylamino-1,3-diazacycloalkenes | |
| AT206891B (en) | Process for the preparation of new tertiary amines | |
| DD140041B1 (en) | METHOD FOR THE PRODUCTION OF LONG-CHAINED N-ALKYLDIMETHYLMORPHOLINES | |
| CH484070A (en) | Process for the preparation of basic substituted phenylacetonitriles | |
| AT206892B (en) | Process for the preparation of new tertiary amines | |
| AT233538B (en) | Process for the preparation of new farnesyl compounds | |
| DE1468167B2 (en) | BASIC ESTERS OF BICYCLIC DICARBONIC ACIDS, THEIR ACID ADDITIONAL SALTS AND BISQUATERNAL AMMONIUM COMPOUNDS, AND PROCESS FOR THE PREPARATION OF THE SAME | |
| CH411847A (en) | Process for the production of camphor derivatives | |
| DE1197887B (en) | Process for the preparation of 3-trifluoromethylphenoxazine derivatives | |
| AT236937B (en) | Process for the production of new basic substituted anthradipyrazoles | |
| AT201582B (en) | Process for the preparation of new dimethylaminopropoxybenzenes | |
| AT204046B (en) | Process for the production of new piperazine derivatives and their salts | |
| AT165072B (en) | Process for the preparation of new pyridinium compounds | |
| AT235286B (en) | Process for the preparation of the new 2- (5 ', 6', 7 ', 8'-tetrahydronaphthyl-1') -amino-imidazoline | |
| AT205031B (en) | Process for the preparation of new, basic substituted derivatives of 4-aza-phenthiazines or their salts | |
| AT280976B (en) | Process for the preparation of new alkylenediamine derivatives and their acid addition salts | |
| AT256823B (en) | Process for the preparation of new heterocyclic benzamido compounds and their salts | |
| AT202147B (en) | Process for the production of new piperazine derivatives and their salts | |
| AT203497B (en) | Process for the production of new diphenylmethane derivatives, their acid salts and quaternary salts | |
| AT220144B (en) | Process for the preparation of new tertiary amines and their acid addition and quaternary ammonium salts | |
| AT231445B (en) | Process for the preparation of new 1, 2, 4-triazolonen- (5) | |
| AT265259B (en) | Process for the preparation of new dextrorotatory and levorotatory forms of 1- (β-hydroxy- or -halo-ethyl) -diphenylmethyl-piperidines and their salts | |
| AT203496B (en) | Process for the preparation of new tertiary amines | |
| AT250960B (en) | Process for the preparation of new derivatives of 7-oxy-2-oxo-1, 2-dihydroquinoline | |
| AT228205B (en) | Process for the preparation of basic phenothiazine derivatives which are substituted in the 3-position by a monovalent sulfur function |