DE588880C - Process for the preparation of 1-phenyl-2-aminopropanolen- (1) in racemic form - Google Patents
Process for the preparation of 1-phenyl-2-aminopropanolen- (1) in racemic formInfo
- Publication number
- DE588880C DE588880C DE1930588880D DE588880DD DE588880C DE 588880 C DE588880 C DE 588880C DE 1930588880 D DE1930588880 D DE 1930588880D DE 588880D D DE588880D D DE 588880DD DE 588880 C DE588880 C DE 588880C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- preparation
- aminopropanolen
- racemic form
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Description
Verfahren zur Darstellung von 1-Phenyl-2-aminopropanolen- (1) in Racemform Durch das Patent 587 586 ist ein Verfahren zur Darstellung von optisch linksdrehenden i-Phenyl-2-aminopropanolen-(i) geschützt, welches darin besteht, daß man optisch linksdrehendes i-Phenyl-2-ketopropanol-(i) in Gegenwart vonAmmoniak oderprimärenAminen der katalytischen Reduktion mit Edelmetallen bzw. in Gegenwart der Salze der genannten Basen der katalytischen Reduktion mit Metallen der Nickelgruppe unterwirft oder daB man optisch linksdrehendes i-Phenyl-z-ketopropanol-(i) mit Hydroxylamin zur Umsetzung bringt und das erhaltene Oxim zu der zugehörigen Aminoverbindung reduziert und gegebenenfalls letztere alkyliert.Process for the preparation of 1-phenyl-2-aminopropanolen- (1) in racemic form By the patent 587 586 is a method for the representation of optically left-handed i-Phenyl-2-aminopropanol- (i) protected, which consists in that one optically levorotatory i-phenyl-2-ketopropanol- (i) in the presence of ammonia or primary amines the catalytic reduction with noble metals or in the presence of the salts mentioned Subjects bases to catalytic reduction with metals of the nickel group or that optically levorotatory i-phenyl-z-ketopropanol- (i) can be mixed with hydroxylamine Bringing reaction and reducing the oxime obtained to the associated amino compound and optionally the latter is alkylated.
Es wurde nun gefunden, daB, wenn man die Reduktion des optisch linksdrehenden Ketoalkohols auf katalytischem Wege mit Metallen der Nickelgruppe in Gegenwart der freien Basen statt ihrer Salze ausführt, die entstandenen Aminoalkohole in Form ihrer Racemverbindungen erhalten werden.It has now been found that if one considers the reduction of the optically left-turning Keto alcohol catalytically with metals of the nickel group in the presence of the carries out free bases instead of their salts, the resulting amino alcohols in the form their racemic compounds are obtained.
Da das verwendete optisch linksdrehende Ketopropanol ein leicht zugänglicher Ausgangsstoff ist, bedeutet das Verfahren einen technischen Fortschritt gegenüber der bisher bekannten Gewinnung der als Heilmittel wichtigen Aminoalkohole.Since the optically left-handed ketopropanol used is an easily accessible one If the starting material is, the process represents a technical advance compared to that the previously known extraction of the amino alcohols important as medicinal products.
Beispiel i 41 .g 1-Phenylacetylcarbinol werden in 42 g einer 2o°/oigen alkoholischen Methylaminlösung gelöst und nach Zusatz von Zoo ccm Alkohol-mit Nickel und Wasserstoff hydriert. Nach kurzer Zeit ist die berechnete Menge Wasserstoff aufgenommen. Man saugt alsdann vom Katalysator ab und destilliert den überschüssigen Alkohol im Vakuum ab. Der verbleibende Rückstand wird in trockenem Äther aufgenommen und durch Einleiten von Salzsäuregas das racemische Phenylpropanolinethylaminhydrochlorid ausgefällt. Das Salz zeigt nach dem Umkristallisieren aus Alkohol den Schmelzunkt 1980. Ausbeute quantitativ.Example i 41 g of 1-Phenylacetylcarbinol are in 42 g of a 20% alcoholic methylamine solution dissolved and after addition of zoo ccm alcohol-with nickel and hydrogenated hydrogen. After a short time the calculated amount is hydrogen recorded. The catalyst is then filtered off with suction and the excess is distilled Alcohol in a vacuum. The remaining residue is taken up in dry ether and by introducing hydrochloric acid gas, the racemic phenylpropanolinethylamine hydrochloride failed. The salt shows the melting point after recrystallization from alcohol 1980. Quantitative yield.
Man gelangt zu demselben Ergebnis, wenn man an Stelle einer alkoholischen Lösung mit einer wässerigen Methylaminlösung und in entsprechender Verdünnung mit Wasser als Lösungsmittel arbeitet.One arrives at the same result if one takes the place of an alcoholic one Solution with an aqueous methylamine solution and diluted accordingly with Water works as a solvent.
Beispiel z 15 g 1-Phenylacetylcarbinol werden in Zoo ccm Alkohol gelöst, mit i i g Benzylamin versetzt und mit Nickel und Wasserstoff hydriert. Die Aufarbeitung wie in Beispiel i ergibt racemisches Phenylbenzylaminopropanolhydrochlorid vom Schmelzpunkt 192 bis 193° Beispiel 3 15 g 1-Phenylacetylcarbinol werden in 25o ccm Methylalkohol gelöst und 15 g einer 2o °higen alkoholischen Ammoniaklösung zugegeben. Die Hydrierung mit Nickel und Wasserstoff und. Aufarbeitung wie in Beispiel i ergibt racemisches Phenylaminopropanolhydrochlorid, das nach dem Umkristallisieren aus Alkohol den Schmelzpunkt 193 bis I94° zeigt.Example z 15 g of 1-phenylacetylcarbinol are dissolved in zoo cc alcohol, mixed with i i g of benzylamine and hydrogenated with nickel and hydrogen. The work-up as in Example i gives racemic melting point phenylbenzylaminopropanol hydrochloride 192 to 193 ° Example 3 15 g of 1-phenylacetylcarbinol are dissolved in 250 cc of methyl alcohol dissolved and added 15 g of a 20 ° alcoholic ammonia solution. The hydrogenation with nickel and hydrogen and. Working up as in Example i gives racemic Phenylaminopropanol hydrochloride, which after recrystallization the end Alcohol has a melting point of 193-194 °.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE588880T | 1930-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE588880C true DE588880C (en) | 1933-11-29 |
Family
ID=6572461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930588880D Expired DE588880C (en) | 1930-09-19 | 1930-09-19 | Process for the preparation of 1-phenyl-2-aminopropanolen- (1) in racemic form |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE588880C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7414153B2 (en) | 2004-04-15 | 2008-08-19 | Emmellen Biotech Pharmaceuticals Limited | Process for preparation of optically active 1-erythro-2-amino-1-phenyl-1-propanol |
| EP2055379A1 (en) * | 2007-10-29 | 2009-05-06 | Emmellen Biotech Pharmaceuticals Ltd. | Raney-nickel-iron catalyst, its preparation and a method to produce L-norephedrine by hydrogenating L-phenylacetylcarbinol-oxime with said catalyst |
-
1930
- 1930-09-19 DE DE1930588880D patent/DE588880C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7414153B2 (en) | 2004-04-15 | 2008-08-19 | Emmellen Biotech Pharmaceuticals Limited | Process for preparation of optically active 1-erythro-2-amino-1-phenyl-1-propanol |
| EP2055379A1 (en) * | 2007-10-29 | 2009-05-06 | Emmellen Biotech Pharmaceuticals Ltd. | Raney-nickel-iron catalyst, its preparation and a method to produce L-norephedrine by hydrogenating L-phenylacetylcarbinol-oxime with said catalyst |
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