CH155346A - Process for the preparation of 1- (3'.4'-Dioxy-phenyl) -2-methylaminopropan-1-ol. - Google Patents
Process for the preparation of 1- (3'.4'-Dioxy-phenyl) -2-methylaminopropan-1-ol.Info
- Publication number
- CH155346A CH155346A CH155346DA CH155346A CH 155346 A CH155346 A CH 155346A CH 155346D A CH155346D A CH 155346DA CH 155346 A CH155346 A CH 155346A
- Authority
- CH
- Switzerland
- Prior art keywords
- dibenzyloxy
- dioxy
- preparation
- phenyl
- halogenation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims 3
- 238000005658 halogenation reaction Methods 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- DLVOBILBYOTEEP-UHFFFAOYSA-N n-[(2-methylphenyl)methyl]propanamide Chemical compound CCC(=O)NCC1=CC=CC=C1C DLVOBILBYOTEEP-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 3
- -1 bromine compound Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von<B>1-(3'.</B> 4:'-]Dioxy-phenjv)-2-methylaininopropaii-l-oi. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1- (3'. 4-Dioxy-phenyl)-2-methylamino-propan -1- ol, welches dadurch gekennzeichnet ist, dass man 3.4-Dibenzyl-oxy-pi#opiophenon haloge- niert, das erhaltene halogenierte Produkt mit Methylbenzylamin umsetzt und das so erhal tene 1-(3'.4'-Dibenzyloxy-pheriyl)
-2-methyl- bei)zylamino-propan-l-on mit reduzierenden Mitteln behandelt.
Das bisher nicht bekannte Verfahrenspro dukt hat adrerialinartige Wirkung und kann entsprechende Anwendung in der Therapie finden. Sein Hydrochlorid hat den Schmelz punkt<B>190-1910 C.</B>
<I>Beispiel:</I> 34,6 gr 3.4-Dibeiizyloxy-pi#opiophenon werd<B>'</B> en in<B>800</B> em3 Methylenchlorid gelöst und nach Zugabe von 12 gr Caleiumcarbonat unter Rühren<B>16</B> gr Brom eitigetropft. Nach beendigter Umsetzung wird vom Ca-Nieder- schlag abfiltriert und die Methylenchlorid- Lösung vollständig eingedampft. Beim Er kalten kristallisiert aus deni Rückstand das
3.4-Dibenzyloxy-brompropiopbenon aus, das nach dem Umkristallisieren aus Hexahydro- benzol oder aus Alkohol bei 93-94<B>0</B> eschrnilzt. <B>30</B> gr der so erhaltenen kristallisierten Brom- Verbindung werden nun in<B>60</B> em3 Alkohol gelöst und mit<B>17</B> gr Methylbenzylamin kurze Zeit auf dem Wasserbad erwärmt. Nach mehrstündigem Stehen wird das aus geschiedene Methylbenzylamin-bromhydrat ab gesaugt und die alkoholische Lösung einge dampft.
Man nimmt den Rückstand in Ätlier auf, filtriert und fällt durch gasförmige Salz säure das sich zuerst als<B>01</B> abscheideiide Chlorhydrat aus. Bei Zugabe von Aceton erbält man eine kristalline Masse, die aus Aceton umkristallisiert bei<B>170</B> 11 schmilzt. Das erhaltene 3.4-Diberizyloxy-methylbenzyl- amino-propiophenon-chlorhydrat wird alsdarin in absolutem Alkohol aufgelöst und mit Pal- ladium und Wasserstoff hydriert.
Nach Auf nahme der berechneten Menge Wasserstoff wird vom Palladium abgesaugt und die al koholische Lösung im Vakuum eingedampft. Der Rückstand wird kristallin und man er hält das 3.4-Dioxy-phenyl-methylamino-pro- panol-chlorhydrat durch Umkristallisieren aus Alkohol unter Zugabe von Äther in reiner Form. Schmelzpunkt 190-19111 <B>C.</B>
Das als Ausgangsmaterial verwendete 3.4- Dibenzyloxy-propiophenon wird in derWeise erhalten, dass man<B>166</B> gr Propiobrenzkate- chin und<B>350</B> gr Benzylbromid in<B>1000</B> em-3 einer 12%igen alkoholischen Kalilauge ein- trägt. Nach ca. zweistündigem Erhitzen auf dem Wasserbade
wird noch heiss durch Zu gabe von Wasser, das bei derReaktion ent standene Bromkali in Lösung gebracht. Beim Abkühlen luistallisiert die Dibenzyl-Verbin- dung aus, die nach dem Umkristallisieren aus Hexahydrobenzol bei<B>66 0</B> schmilzt.
Method for the preparation of <B> 1- (3 '. </B> 4:' -] Dioxy-phenjv) -2-methylaininopropaii-l-oi. The present invention relates to a process for the preparation of 1- (3 '. 4-dioxy-phenyl) -2-methylamino-propan -1-ol, which is characterized in that 3,4-dibenzyl-oxy-pi # opiophenone is halogenated - nated, the halogenated product obtained is reacted with methylbenzylamine and the 1- (3'.4'-dibenzyloxypheriyl) obtained
-2-methyl- bei) zylamino-propan-l-one treated with reducing agents.
The previously unknown process product has an adrerialin-like effect and can be used in therapy. Its hydrochloride has a melting point of <B> 190-1910 C. </B>
<I> Example: </I> 34.6 g 3.4-dibeiizyloxy-pi # opiophenone are <B> '</B> s dissolved in <B> 800 </B> em3 methylene chloride and, after adding 12 g calcium carbonate, under Stir <B> 16 </B> g bromine added dropwise. After the reaction has ended, the calcium precipitate is filtered off and the methylene chloride solution is completely evaporated. When cold, the residue crystallizes from the residue
3.4-dibenzyloxy-bromopropiopbenone, which after recrystallization from hexahydrobenzene or from alcohol melts at 93-94 <B> 0 </B>. <B> 30 </B> g of the crystallized bromine compound obtained in this way are now dissolved in <B> 60 </B> em3 alcohol and heated for a short time on the water bath with <B> 17 </B> g of methylbenzylamine. After standing for several hours, the separated methylbenzylamine bromohydrate is sucked off and the alcoholic solution is evaporated.
The residue is taken up in Etlier, filtered and precipitated by gaseous hydrochloric acid which first separates out as hydrochloride. When acetone is added, a crystalline mass is obtained which, recrystallized from acetone, melts at <B> 170 </B> 11. The 3,4-diberizyloxymethylbenzylamino-propiophenone chlorohydrate obtained is then dissolved in absolute alcohol and hydrogenated with palladium and hydrogen.
After taking on the calculated amount of hydrogen, the palladium is sucked off and the alcoholic solution evaporated in vacuo. The residue becomes crystalline and the 3,4-dioxyphenyl-methylamino-propanol chlorohydrate is kept in pure form by recrystallization from alcohol with the addition of ether. Melting point 190-19111 C.B.
The 3,4-dibenzyloxy-propiophenone used as starting material is obtained in such a way that <B> 166 </B> gr propiobrenzkatequin and <B> 350 </B> gr benzyl bromide in <B> 1000 </B> em- 3 of a 12% alcoholic potassium hydroxide solution. After about two hours of heating on the water bath
If it is still hot, the addition of water dissolves the potassium bromide formed during the reaction. On cooling, the dibenzyl compound crystallizes out, which, after recrystallization from hexahydrobenzene, melts at <B> 66 0 </B>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE155346X | 1929-12-06 | ||
| CH153036T | 1931-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155346A true CH155346A (en) | 1932-06-15 |
Family
ID=25716115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155346D CH155346A (en) | 1929-12-06 | 1930-12-05 | Process for the preparation of 1- (3'.4'-Dioxy-phenyl) -2-methylaminopropan-1-ol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155346A (en) |
-
1930
- 1930-12-05 CH CH155346D patent/CH155346A/en unknown
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