CH451115A - Process for the preparation of a new amine - Google Patents
Process for the preparation of a new amineInfo
- Publication number
- CH451115A CH451115A CH1213767A CH1213767A CH451115A CH 451115 A CH451115 A CH 451115A CH 1213767 A CH1213767 A CH 1213767A CH 1213767 A CH1213767 A CH 1213767A CH 451115 A CH451115 A CH 451115A
- Authority
- CH
- Switzerland
- Prior art keywords
- salts
- preparation
- acid
- allyloxyphenol
- isopropylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001412 amines Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 9
- FNEJKCGACRPXBT-UHFFFAOYSA-N 2-prop-2-enoxyphenol Chemical compound OC1=CC=CC=C1OCC=C FNEJKCGACRPXBT-UHFFFAOYSA-N 0.000 claims description 5
- -1 3-isopropylamino-2-hydroxypropyl halide Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- FTJSDHRLVNMSLN-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(4-prop-2-enoxyphenoxy)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(OCC=C)C=C1 FTJSDHRLVNMSLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- AQFROTXMDPNEJE-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)propan-2-amine Chemical compound CC(C)NCC1CO1 AQFROTXMDPNEJE-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- ZRBLAFWOGCBZPV-UHFFFAOYSA-N 1-chloro-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)CCl ZRBLAFWOGCBZPV-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 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
- 239000001294 propane Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Amins
Gegenstand der Erfindung ist ein Verfahren zur Herstellung des 1-Isopropylamino-2-hydroxy-3- (o-all'lyl- oxyphenoxy)-propans der Formel
EMI1.1
Die neue Verbindung besitzt wertvolle pharmakolo gische Eigenschaften. Insbesondere bewirkt sie eine Hemmung adrenergischer ¯-Rezeptoren. Sie kann dementsprechend bei Herz-und Kreislauferkrankungen ais Medikament angewendet werden.
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindung ist dadurch gekennzeichnet, dass man o-Allyloxy-phenol mit einer Verbindung der all gemeinen Formel
EMI1.2
worin X2 eine Hydroxylgruppe und'Xi eine reaktionsfä'hig veresterte Hydroxylgruppe bedeulten oder Xi und XO gemeinsam eine Sauerstoffbrücke bilden, umsetzt.
Dabei kann man in üblicher Weise arbeiten. Ein reak tionsfähiger Ester ist d'abei z. B. derjenige einer starken organischen oder anorganischen Säure, wie vor allem einer Halogenwasserstoffsäure, z. B. der Chlor-, Bromoder Jodwasserstoffsäure, oder einer Sulfonsäure, wie einer ArylsulfonsÏure, z. B. der p-Toluolsulfonsäure. Bei Verwendung der Ester verfährt man zweckmässig in Gegenwart eines säurebindenden Kondensationsmittels, insbesondere eines zur Salzbildung mit dem Phenol geeigneten Kondensationsmittels, oder man verwendet ein Metallsalz, wie Alkalisalz, des Phenols. So kann man in Gegenwart von Alkalialkoholaten arbeiten.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden.
Je nach den Verfahrensbedingungen und Ausgangs- stoffen erhält man den Endstoff in freier Form oder in der ebenfalls in der Erfindung inibegriffenen Form seiner Salze. Die Salze des Endstoffes können in an sich bekannter Weise, z. B. mit Alkalien oder Ionenaustau- schern, in die freie Base übergeführt werden. Von der letzteren lassen sich durch Umsetzung mit organischen oder anorganischen Säuren, insbesondere solchen, die zur Bildung von therapeutisch verwendbaren Salzen geeignet sind, Salze gewinnen.
Als solche Säuren seien beispielsweise genannt :
HalogenwasserstoffsÏuren, Schwefelsäwren,
PhosphorsÏuren, SalpetersÏure, PerchlorsÏure, aliphatiscbe, alicyclische, aromatische oder heterocyclische Carbon-oder Sulfonsäuren, wie
Ameisen-, Essig-, Propion-, Bernstein-, Glykol-,
Milch-, ¯pfel-, Wein-, Zitronen-, Ascorbin-,
Malein-, Hydroxymalein- oder BrenztraubensÏure ;
Phenylessig-, Benzoe-, p-Aminobenzoe-, Anthranil-, p-Hydroxy-benzoe-, Salicyl-oder p-Aminosalicyl-sÏure, EmbonsÏure, Methansulfon-, Äthansulfon-, Hydroxyäthansulfon-, ¯thylensulfonsÏure ;
Halogenbenzolsulfon-, Toluolsulfon-,
Naphthalinsulfonsäure oder Sulfanilsäure ;
Methionin, Tryptophan, Lysin oder Arginin.
Diese oder andere Salze der neuen Verbindung, wie z. B. die Pirate, können auch zur Reinigung der erhal- tenen freien Base dienen, indem man die freie Base in Salze überführt, diese abtrennt und aus den Salzen wiederum d'ie Base freimacht. Infolge der engen Beziehun- gen zwischen der neuen Verbindung in freier Form und in Form ihrer Salze sind im Vorausgegangenen und nachfolgend unter der freien Base sinn-und zweckmässig gegebenenfalls auch die entsprechenden Salze zu verstehen.
Die neue Verbindung kann als Racemat oder in Form der Antipoden vorliegen. Das Racemat kann in üblicher Weise in die Antipoden zerlegt werden.
Die neue Verbindung kann z. B. in Form pharma- zeutischer Präparate Verwendung finden, welche sie in freier Form oder gegebenenfalls in Form ihrer Salze in Mischung mit einem für die enterale oder parenterale Applikation geeigneten pharmazeutischen, organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten.
Im folgenden Beispiel werden die Temperaturen in Celsiusgraden angegeben.
Beispiel
20 g o-Allyloxy-phenol, 15 g 3-Isopropylamino-2 hydroxy-l-chl'orpropan und 20 g fein gemahlene Pott- asche werden in 300 ml Aceton während 5 Stunden bei 50 gerührt. Den ungelösten Anteil filtriert man ab und dampft die Aceton-Lösung im Wasserstrahlvakuum ein.
Der Rückstand wird in Ather gelöst und mit 2n Natronlauge extrahiert. Die ¯therschicht trennt man ab und dampft zur Trockne ein. Es verbleibt das 1-Isopropyl- amino-2-hydroxy-3- (o-allyloxy-phenoxy)-propan der Formel
EMI2.1
das nach Sublimation bei 78-81¯ schmilzt. Das Hydrochlorid schmilzt bei 107-109¯.
Process for the preparation of a new amine
The invention relates to a process for the preparation of 1-isopropylamino-2-hydroxy-3- (o-all'lyl oxyphenoxy) propane of the formula
EMI1.1
The new compound has valuable pharmacological properties. In particular, it inhibits adrenergic ¯ receptors. Accordingly, it can be used as a drug for cardiovascular diseases.
The inventive method for the preparation of the new compound is characterized in that o-allyloxyphenol with a compound of the general formula
EMI1.2
wherein X2 is a hydroxyl group and Xi is a reactive esterified hydroxyl group or Xi and XO together form an oxygen bridge.
You can work in the usual way. A reactive ester is here for. B. that of a strong organic or inorganic acid, such as especially a hydrohalic acid, e.g. B. the chlorine, bromine or hydroiodic acid, or a sulfonic acid, such as an ArylsulfonsÏure, z. B. p-toluenesulfonic acid. When using the esters, the procedure is expediently in the presence of an acid-binding condensing agent, in particular a condensing agent suitable for salt formation with the phenol, or a metal salt, such as an alkali metal salt, of phenol is used. So you can work in the presence of alkali metal alcoholates.
The starting materials are known or can be obtained by methods known per se.
Depending on the process conditions and starting materials, the end product is obtained in free form or in the form of its salts, which is also included in the invention. The salts of the end product can in a manner known per se, for. B. with alkalis or ion exchangers, are converted into the free base. Salts can be obtained from the latter by reaction with organic or inorganic acids, in particular those which are suitable for the formation of therapeutically useful salts.
Examples of such acids are:
Hydrogen halides, sulfuric acids,
Phosphoric acids, nitric acid, perchloric acid, aliphatic, alicyclic, aromatic or heterocyclic carboxylic or sulfonic acids, such as
Ant, vinegar, propion, amber, glycol,
Milk, apple, wine, lemon, ascorbic,
Maleic, hydroxymaleic or pyruvic acid;
Phenylacetic, benzoic, p-aminobenzoic, anthranil, p-hydroxy-benzoic, salicylic or p-aminosalicylic acid, embonic acid, methanesulphonic, ethanesulphonic, hydroxyethanesulphonic, ¯thylenesulphonic acid;
Halobenzenesulfone, toluenesulfone,
Naphthalenesulfonic acid or sulfanilic acid;
Methionine, tryptophan, lysine or arginine.
These or other salts of the new compound, such as. B. the pirates, can also be used to purify the free base obtained by converting the free base into salts, separating them and in turn frees the base from the salts. As a result of the close relationships between the new compound in free form and in the form of its salts, in the preceding and in the following the free base is to be understood meaningfully and expediently also the corresponding salts.
The new compound can be present as a racemate or in the form of the antipodes. The racemate can be broken down into the antipodes in the usual way.
The new connection can e.g. B. in the form of pharmaceutical preparations are used which they contain in free form or optionally in the form of their salts mixed with a pharmaceutical, organic or inorganic, solid or liquid carrier material suitable for enteral or parenteral administration.
In the following example the temperatures are given in degrees Celsius.
example
20 g of o-allyloxyphenol, 15 g of 3-isopropylamino-2-hydroxy-1-chloropropane and 20 g of finely ground potash are stirred in 300 ml of acetone at 50 for 5 hours. The undissolved portion is filtered off and the acetone solution is evaporated in a water jet vacuum.
The residue is dissolved in ether and extracted with 2N sodium hydroxide solution. The ether layer is separated and evaporated to dryness. What remains is the 1-isopropylamino-2-hydroxy-3- (o-allyloxyphenoxy) propane of the formula
EMI2.1
which melts at 78-81¯ after sublimation. The hydrochloride melts at 107-109¯.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1213767A CH451115A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of a new amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1213767A CH451115A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of a new amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH451115A true CH451115A (en) | 1968-05-15 |
Family
ID=4380230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1213767A CH451115A (en) | 1964-09-10 | 1964-09-10 | Process for the preparation of a new amine |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH451115A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005192A1 (en) * | 1978-04-29 | 1979-11-14 | BASF Aktiengesellschaft | Alkylaminopropanol derivatives of 3-alkyl-5-(2-hydroxystyryl)-isoxazoles, processes for their preparation and therapeutical compositions containing them |
| US4305951A (en) | 1979-10-26 | 1981-12-15 | Basf Aktiengesellschaft | Novel amino derivatives of 5-(2-hydroxystyryl)-isoxazole, their preparation and therapeutic formulations containing these compounds |
-
1964
- 1964-09-10 CH CH1213767A patent/CH451115A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005192A1 (en) * | 1978-04-29 | 1979-11-14 | BASF Aktiengesellschaft | Alkylaminopropanol derivatives of 3-alkyl-5-(2-hydroxystyryl)-isoxazoles, processes for their preparation and therapeutical compositions containing them |
| US4305951A (en) | 1979-10-26 | 1981-12-15 | Basf Aktiengesellschaft | Novel amino derivatives of 5-(2-hydroxystyryl)-isoxazole, their preparation and therapeutic formulations containing these compounds |
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