DE241425C - - Google Patents
Info
- Publication number
- DE241425C DE241425C DENDAT241425D DE241425DA DE241425C DE 241425 C DE241425 C DE 241425C DE NDAT241425 D DENDAT241425 D DE NDAT241425D DE 241425D A DE241425D A DE 241425DA DE 241425 C DE241425 C DE 241425C
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydroisoquinoline
- methylal
- phenylethylamine
- solution
- derivatives
- 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.)
- Active
Links
- BHHGXPLMPWCGHP-UHFFFAOYSA-N 2-Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 4
- NKDDWNXOKDWJAK-UHFFFAOYSA-N Dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N Tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OXFGRWIKQDSSLY-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-2-ium-1-carboxylate Chemical compound C1=CC=C2C(C(=O)O)NCCC2=C1 OXFGRWIKQDSSLY-UHFFFAOYSA-N 0.000 description 1
- BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 description 1
- HQVFWMFRDZKLPB-UHFFFAOYSA-N 6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinoline Chemical compound C1CNCC2=C(OCO3)C3=CC=C21 HQVFWMFRDZKLPB-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- RRIRDPSOCUCGBV-UHFFFAOYSA-N Methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 description 1
- 229960005190 Phenylalanine Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE Up: GRUPPECLASS Up: GROUP
Dr. AME PICTETiN GENF.Dr. AME PICTETiN GENEVA.
Verfahren zur Herstellung von Tetrahydroisochinolin und Derivaten desselben. Patentiert im Deutschen Reiche vom 9. April 1911 ab.Process for the preparation of tetrahydroisoquinoline and derivatives thereof. Patented in the German Empire on April 9, 1911.
Die Erfindung beruht auf der Beobachtung, dessen Substitutionsprodukten unter Bildung 35 daß Methylal in Gegenwart konzentrierter von Tetrahydroisochinolin oder Derivaten des-Mineralsäuren sich mit Phenyläthylamin oder | selben kondensieren läßt, z. B.The invention is based on the observation, the substitution products of which with formation 35 that methylal in the presence of concentrated tetrahydroisoquinoline or derivatives of mineral acids with phenylethylamine or | same can condense, z. B.
CH9 CH 9
CH9 CH 9
CH,CH,
2 +C HZ(OC H3J2 = 2 + CH Z (OC H 3 J 2 =
NH9 NH 9
CH2 CH 2
NHNH
zCH^OH.zCH ^ OH.
CH0 CH 0 4040
4545
Beispiel I.
Herstellung von Tetrahydroisochinolin.Example I.
Manufacture of tetrahydroisoquinoline.
2 Teile Phenyläthylamin (oder dessen Chlorhydrat) werden in io Teilen konzentrierter Salzsäure gelöst, mit ι Teil Methylal, versetzt und 6 Stunden auf dem Wasserbade unter Rückfluß erwärmt. Die Lösung wird dann zur Trockne verdampft, das zurückbleibende Chorhydrat durch Alkali zersetzt und das freie Hydroisochinolin durch fraktionierte Destillation oder über das Nitrosamin gereinigt. Es bildet eine farblose Flüssigkeit vom Kp. 2300.2 parts of phenylethylamine (or its chlorohydrate) are dissolved in 10 parts of concentrated hydrochloric acid, 1 part of methylal is added and the mixture is heated under reflux on a water bath for 6 hours. The solution is then evaporated to dryness, the remaining chlorohydrate is decomposed by alkali and the free hydroisoquinoline is purified by fractional distillation or via the nitrosamine. It forms a colorless liquid with a boiling point of 230 0 .
Beispiel II. Herstellung des Norhydrohydrastinins (6 · 7 - Methylendioxytetrahydroisochinolin).Example II. Preparation of norhydrohydrastinine (6 x 7-methylenedioxytetrahydroisoquinoline).
C H9 CH 9
5555
6060
CH9 CH 9
In ganz derselben Weise erhält man die genannte Verbindung, wenn man im vorangehenden Beispiel das Phenyläthylamin durch j Druck siedet, dar. Homopiperonylamin ersetzt. Sie stellt eine farblose Flüssigkeit, die bei 198° unter 50 mmThe connection mentioned is obtained in exactly the same way if one in the preceding Example that phenylethylamine boils under pressure. Replaced homopiperonylamine. It represents a colorless liquid that is below 50 mm at 198 °
6565
Beispiel III.
Herstellung von Tetrahydroisochinolin - 3 - carbonsäure.Example III.
Production of tetrahydroisoquinoline - 3 - carboxylic acid.
CH.COOH NHCH.COOH NH
ι Teil Phenylalanin wird mit 1 Teil Methylal und 10 Teilen konzentrierter Salzsäure 6 Stunden auf dem Wasserbade unter Rückfluß erwärmt und die Lösung zur Trockne verdampft. Der Rückstand wird in Ammoniak aufgenommen, die Lösung kurze Zeit aufgekocht und mit einer wäßrigen Lösung von Kupferacetat oder -sulfat versetzt. Das dabei ausfallende blaue Kupfersalz der Tetrahydroisochinolincarbonsäure wird abfiltriert und durch Schwefelwasserstoff zersetzt. Die freie Säure kristallisiert aus ihrer wäßrigen Lösung durch Zusatz von Alkohol in farblosen, bei schmelzenden Blättchen.ι part of phenylalanine is mixed with 1 part of methylal and 10 parts of concentrated hydrochloric acid for 6 hours on the water bath under reflux heated and the solution evaporated to dryness. The residue is dissolved in ammonia taken up, the solution boiled for a short time and mixed with an aqueous solution of copper acetate or sulfate. That thereby precipitating blue copper salt of tetrahydroisoquinoline carboxylic acid is filtered off and decomposed by hydrogen sulfide. The free acid crystallizes from its aqueous solution by adding alcohol in colorless, melting leaves.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE241425C true DE241425C (en) |
Family
ID=500721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT241425D Active DE241425C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE241425C (en) |
-
0
- DE DENDAT241425D patent/DE241425C/de active Active
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