CH150921A - Process for the preparation of racemic phenylpropanolphenylpropanonmethylamine. - Google Patents
Process for the preparation of racemic phenylpropanolphenylpropanonmethylamine.Info
- Publication number
- CH150921A CH150921A CH150921DA CH150921A CH 150921 A CH150921 A CH 150921A CH 150921D A CH150921D A CH 150921DA CH 150921 A CH150921 A CH 150921A
- Authority
- CH
- Switzerland
- Prior art keywords
- ephedrine
- racemic
- parts
- preparation
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229960002179 ephedrine Drugs 0.000 claims description 11
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von racemischem Phenylpropanolphenylpropanoiimethylamin. Es wurde gefunden, dass sich Ephedrin mit 1-Phenyl-l-oxo-2-bronipropati (a-Brom- propiophenon) leicht gemäss nachstehender Gleichung zu racemischen Phenylpropanol- phenylpropanonmethylamin umsetzt:
'
EMI0001.0011
Die Umsetzung ka-nn dadurch erreicht werden, dass man einen Überschuss von Ephe- drin mit 1-Phenyl-l-oxo-2-brompropan (a- Brompropiophenon) zusammenbringt. Statt einen Überschuss von Ephedrin zu verwen den, kann man die Kandensation mit Alka-li bewirken.
Das racemische Phenylpropanolphenyl- pro,panonmetliylamin ist in den üblichen organischen Lösungsmitteln, wie Alkohol., Äther, Benzol', Chloroform, löslich, unlös lich in Wasser. Es schmilzt bei<B>92</B> bis <B>93 '</B> und ist optisch inaktiv. Das Hydro- ehlorid ist sehr leicht löslich in Wasser und Alkahol und schmilzt bei 194'.
Die neue Verbindung soll als solche thera peutische Verwendung finden oder als Zwi schenprodukt zur Herstellung pharmazeuti scher Präparate dienen.
<I>Beispiel<B>1:</B></I> 20 Teile racemisches Ephedrin werden fünf Stunden mit 112 Teilen a-Brompropio- phenon in<B>100</B> Teilen Benzol gekocht. Dann werden die Basen mit Säure ausgeehüttelt, die saure Lösung alkalisch gemacht, aus- geäthert und derltherrückstand imVakuum destilliert, wobei das unveränderte Ephedrin wieder gewonnen wird.
Der Rückstand, aus Met11ylalkohol umkristallisiert, g#ibt das racemisolie Phenylpropanolpheilylpropanon- methylamin vom Schmelzpankt <B>92</B> bis<B>93</B> <I>Beispiel 2:</I> <B>16</B> Teile 1-Ephedrin werden in<B>80</B> Teilen Benzol fünf Stunden mit 12 Teilen 1-Phenyl- l#-oxo-2#brompxopan (#-Brompropiophenon.) gekocht.
Dann wird ohne Rücksiellt auf aus gefallenes Ephedrinsalz das Reaktions- gemisell mit Säure behandelt, 9,lkaliseh ge macht und ausgeätll#ert. Das unveränderte Ephedrin wird durch Vakuumdestillation entfernt und der Rückstand aus Methyl- alkoliol umkristallisiert. Das so erhaltene Kondensa;tionsprodukt- schmilzt bei<B>92</B> bis <B>93'.</B> Es ist- optisch inaktiv.
<I>Beispiel<B>3:</B></I> <B>33</B> Teile 1-Ephedrinba.se werden in<B>100</B> Teilen Benzol und<B>100</B> Teilen Wasser mit 43 Teilen a-Brompropiophenon mittelst 1.2 Teilen Kaliumhydroxyd kondensiert; die Basen werden in Säure aufgenommen, alka- lisell gemacht und ausgeithert. Der Äther rückstand liefert neben wenig unveränder tem Ephedrin, das abdestilliert wird, in einer Ausbeute von<B>26</B> Teilen den im Beispiel 2 beschriebenen, optisch inaktiven Körper vom Schmelzpunkt<B>92</B> bis<B>93</B> '.
Process for the preparation of racemic phenylpropanolphenylpropanoiimethylamine. It has been found that ephedrine reacts easily with 1-phenyl-l-oxo-2-bronipropati (a-bromopropiophenone) to form racemic phenylpropanol-phenylpropanonmethylamine according to the following equation:
'
EMI0001.0011
The reaction can be achieved by combining an excess of ephe- drine with 1-phenyl-1-oxo-2-bromopropane (a-bromopropiophenone). Instead of using an excess of ephedrine, one can effect the candensation with Alka-li.
The racemic Phenylpropanolphenylpro, panonmetliylamin is in the usual organic solvents such as alcohol., Ether, Benzene ', chloroform, soluble, insoluble Lich in water. It melts at <B> 92 </B> to <B> 93 '</B> and is optically inactive. The hydrochloride is very easily soluble in water and alcohol and melts at 194 °.
The new compound should find therapeutic use as such or serve as an inter mediate product for the manufacture of pharmaceutical preparations.
<I> Example <B>1:</B> </I> 20 parts of racemic ephedrine are boiled for five hours with 112 parts of a-bromopropiophenone in 100 parts of benzene. Then the bases are shaken out with acid, the acidic solution is made alkaline, etherified and the residue is distilled in vacuo, whereby the unchanged ephedrine is recovered.
The residue, recrystallized from methyl alcohol, gives the racemisole phenylpropanolpheilylpropanonmethylamine with a melting range <B> 92 </B> to <B> 93 </B> <I> Example 2: </I> <B> 16 </ B> Parts of 1-ephedrine are boiled in <B> 80 </B> parts of benzene for five hours with 12 parts of 1-phenyl-1 # -oxo-2 # brompxopan (# -bromopropiophenone.).
Then the reaction gemisell is treated with acid, without leaving any residue on the precipitated ephedrine salt, rendered alkaline and excreted. The unchanged ephedrine is removed by vacuum distillation and the residue is recrystallized from methyl alcohol. The condensation product obtained in this way melts at <B> 92 </B> to <B> 93 '. </B> It is - optically inactive.
<I>Example<B>3:</B> </I> <B> 33 </B> parts 1-Ephedrinba.se are converted into <B> 100 </B> parts benzene and <B> 100 </ B> parts of water with 43 parts of a-bromopropiophenone condensed with 1.2 parts of potassium hydroxide; the bases are taken up in acid, made alkaline and expanded. The ether residue provides, in addition to little unchanged ephedrine, which is distilled off, in a yield of <B> 26 </B> parts the optically inactive body described in Example 2 with a melting point of <B> 92 </B> to <B> 93 </B> '.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE150921X | 1930-01-18 | ||
| DE210230X | 1930-02-21 | ||
| DE260630X | 1930-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH150921A true CH150921A (en) | 1931-11-30 |
Family
ID=27180738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH150921D CH150921A (en) | 1930-01-18 | 1930-12-10 | Process for the preparation of racemic phenylpropanolphenylpropanonmethylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH150921A (en) |
-
1930
- 1930-12-10 CH CH150921D patent/CH150921A/en unknown
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