CH100876A - Process for the preparation of 3,5 dibromo-p-oxyphenylethylamine. - Google Patents
Process for the preparation of 3,5 dibromo-p-oxyphenylethylamine.Info
- Publication number
- CH100876A CH100876A CH100876DA CH100876A CH 100876 A CH100876 A CH 100876A CH 100876D A CH100876D A CH 100876DA CH 100876 A CH100876 A CH 100876A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- oxyphenylethylamine
- dibromo
- acetic acid
- glacial acetic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- COESHZUDRKCEPA-ZETCQYMHSA-N 3,5-dibromo-L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC(Br)=C(O)C(Br)=C1 COESHZUDRKCEPA-ZETCQYMHSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010792 warming Methods 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
- C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 3,5 Dibrom-p-Ogyphenyläthylamin. Analog dein Verfahren des Hauptpatentes zur Herstellung von 3,5-Dibromtyrosin gelangt man zu einem dibromierten p-Oxyphenyläthyl- amin, wenn man die Lösung von p-Oxyphenyl- äthylamin in Eisessig mit einer Lösung von Brom in Eisessig behandelt.
Durch Zusatz der berechneten Laugenmenge zur Bindung des Bromwasserstoffs wird aus alkoholischer oder wässeriger Lösung das 3.5-Dibrom-p- Oxyphenyläthylamin in weissen, flachen, rhom bischen Stäbchen, die in Wasser und Wein geist schwer löslich sind, auskristallisiert. Diese Reaktion ist unerwartet, da p-Oxyphenyl- äthylamin gegen unverdünntes Brom sehr empfindlich ist und dabei verharzt. Das durch Einwirkung von Brom in Eisessig entstehende 3,5-Dibrom-p-Oxyphenyläthylamin ist neu.
<I>Beispiel:</I> 2,74 g p-Oxyphenyläthylainin, in 25 cc Eisessig suspendiert, wurden mit einer Lösung von 4 g Brom in 10 cc Eisessig versetzt. Der Bromverbrauch geht unter ziemlicher Er wärmung fast momentan vor sich, es scheidet sich bald bromwasserstoffsaures 3,5-Dibrom- 4 oxyphenyläthylamin in Form kleiner rhom bischer Täfelchen aus. In etwa 1/4 h ist die ganze Flüssigkeit zu einem Kristallbrei- er starrt.
Durch Verdünnen mit Äther und Ab saugen wurden 6,45 g eines farblosen Kristall= Pulvers gewonnen, entsprechend 85,8 % der theoretischen Ausbeute.
Aus dem Filtrate wurden noch 0,3 gr (etwa 4%) isoliert. Nach dem Umkristallisieren aus heissem Methyl alkohol wurde das Hydrobromid in makros- kopischen, 6-teiligen Tafeln vom F.
P.2700 erhalten. Br. gefunden 63,52 % ber. 63,79 %. Das Produkt soll pharmazeutische Verwen dung finden.
EMI0001.0051
Berechnete <SEP> Ausbeute <SEP> 78,5 <SEP> %
<tb> erhalten <SEP> 70,1 <SEP> %
<tb> Br. <SEP> gefunden <SEP> 53,6 <SEP> % <SEP> bei-. <SEP> 54,1 <SEP> %
<tb> N. <SEP> 4,71 <SEP> % <SEP> 4,75 <SEP> % <SEP> Sm. <SEP> 210 <SEP> 0 <SEP> u. <SEP> Z.
Process for the preparation of 3,5 dibromo-p-ogyphenylethylamine. Analogous to the process of the main patent for the production of 3,5-dibromotyrosine, a dibrominated p-oxyphenylethylamine is obtained if the solution of p-oxyphenylethylamine in glacial acetic acid is treated with a solution of bromine in glacial acetic acid.
By adding the calculated amount of lye to bind the hydrogen bromide, the 3,5-dibromo-p-oxyphenylethylamine is crystallized from alcoholic or aqueous solution in white, flat, rhombic rods that are sparingly soluble in water and wine. This reaction is unexpected, since p-oxyphenylethylamine is very sensitive to undiluted bromine and becomes resinous in the process. The 3,5-dibromo-p-oxyphenylethylamine formed by the action of bromine in glacial acetic acid is new.
<I> Example: </I> 2.74 g of p-oxyphenylethylamine, suspended in 25 cc of glacial acetic acid, were mixed with a solution of 4 g of bromine in 10 cc of glacial acetic acid. The bromine consumption is almost instantaneous, with considerable warming, and 3,5-dibromo-4-oxyphenylethylamine hydrobromic acid soon separates out in the form of small rhombic tablets. In about 1/4 hour all of the liquid has solidified into a crystal pulp.
By diluting with ether and sucking off 6.45 g of a colorless crystal powder were obtained, corresponding to 85.8% of the theoretical yield.
0.3 g (about 4%) were isolated from the filtrate. After recrystallization from hot methyl alcohol, the hydrobromide was shown in macroscopic, 6-part plates from F.
P.2700 received. Br. Found 63.52% calc. 63.79%. The product is intended to be used in pharmaceuticals.
EMI0001.0051
Calculated <SEP> yield <SEP> 78.5 <SEP>%
<tb> received <SEP> 70.1 <SEP>%
<tb> Br. <SEP> found <SEP> 53.6 <SEP>% <SEP> at-. <SEP> 54.1 <SEP>%
<tb> N. <SEP> 4.71 <SEP>% <SEP> 4.75 <SEP>% <SEP> Sm. <SEP> 210 <SEP> 0 <SEP> u. <SEP> Z.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH95300T | 1921-03-19 | ||
| CH100876T | 1922-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100876A true CH100876A (en) | 1923-08-16 |
Family
ID=25704954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100876D CH100876A (en) | 1921-03-19 | 1922-04-05 | Process for the preparation of 3,5 dibromo-p-oxyphenylethylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH100876A (en) |
-
1922
- 1922-04-05 CH CH100876D patent/CH100876A/en unknown
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