DE432420C - Process for the preparation of N-methylsulphurous acid salts of secondary amines - Google Patents

Process for the preparation of N-methylsulphurous acid salts of secondary amines

Info

Publication number
DE432420C
DE432420C DEF49555D DEF0049555D DE432420C DE 432420 C DE432420 C DE 432420C DE F49555 D DEF49555 D DE F49555D DE F0049555 D DEF0049555 D DE F0049555D DE 432420 C DE432420 C DE 432420C
Authority
DE
Germany
Prior art keywords
parts
preparation
acid salts
secondary amines
methylsulphurous
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
Application number
DEF49555D
Other languages
German (de)
Inventor
Dr Max Bockmuehl
Dr Kurt Windisch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JG Farbenindustrie AG
Original Assignee
JG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DEF46914D external-priority patent/DE421505C/en
Application filed by JG Farbenindustrie AG filed Critical JG Farbenindustrie AG
Priority to DEF49555D priority Critical patent/DE432420C/en
Application granted granted Critical
Publication of DE432420C publication Critical patent/DE432420C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung von N-methylschwefligsauren Salzen sekundärer Amine. Durch das Hauptpatent ist ein Verfahren geschützt, nach welchem man durch Überführung sekundärer aromatisch-aliphatischer Amine in ihre N-methylschwefligsauren Salze eine bedeutende Steigerung der antipyretischen Wirkung erzielt. Mit dieser Steigerung der antipyretischen Wirkung ist gleichzeitig eine starke Entgiftung verbunden.Process for the preparation of N-methylsulfurous acid salts of secondary Amines. The main patent protects a process by which one can go through Conversion of secondary aromatic-aliphatic amines into their N-methylsulfurous acids Salts achieved a significant increase in the antipyretic effect. With this Increasing the antipyretic effect is linked to a strong detoxification at the same time.

Es wurde nun weiter gefunden, daß man durch Kondensation von Formaldehydbisulfit mit sekundären Aminen mit zyklisch gebundenem Stickstoffatom eine starke Entgiftung der Basen herbeiführen kann, so daß sie mit Vorteil als Arzneimittel und besonders als Antipyretika Anwendung finden können. Beispiele. 1. 6-Methoxytetrahydrochinolinmethansulfosaures Natrium. 163 Teile 6-Methoxytetrahydrochinolin (Thallin),werden in 40o Teilen verdünntem Alkohol gelöst und bei Dampfbadtemperatur eine Formaldehydbisulfitlösung, die z.B. aus 77 Teilen 38,9prozentiger Formaldehydlösung und 272 Teilen 38,3prozentiger Natriumbisulfitlösung bereitet wird, zugesetzt. Die Reaktionslösung erstarrt beim Erkalten feinkristallinisch. Die neue Verbindung wird aus Alkohol oder Methylalkohol umgelöst und zeigt den Schmelzpunkt 226° unter Zersetzung.It has now also been found that condensation of formaldehyde bisulfite with secondary amines with cyclically bound nitrogen atoms a strong detoxification of bases can bring about, so that they can be used with advantage as medicinal products and especially can be used as antipyretics. Examples. 1. 6-methoxytetrahydroquinoline methanesulfonic acid Sodium. 163 parts of 6-methoxytetrahydroquinoline (thallin) are diluted in 40o parts Dissolved alcohol and, at steam bath temperature, a formaldehyde bisulphite solution, e.g. from 77 parts of 38.9 percent formaldehyde solution and 272 parts of 38.3 percent sodium bisulfite solution is prepared, added. The reaction solution solidifies in a finely crystalline manner on cooling. The new compound is dissolved from alcohol or methyl alcohol and shows the melting point 226 ° with decomposition.

2. 23 Teile 8-Oxytetrahydrochinolin (vgl. Ber. 14 [1881] S. 1368) werden mit einer Formaldehydbisulfitlösung, die z. B. aus 11 Teilen 39,7prozentiger Formaldehydlösung und 4o Teilen 38,75prozentiger Natriumbisulfitlösung entsteht, auf dem Dampfbad erhitzt, bis Lösung eintritt. Nach dem Versetzen mit Methylalkohol fällt nach dem Filtrieren Äther den neuen Körper als fast weißes Pulver aus, der sich aus Alkoholäther umlösen läßt.2. 23 parts of 8-oxytetrahydroquinoline (cf. Ber. 14 [1881] p. 1368) are treated with a formaldehyde bisulfite solution, e.g. B. from 11 parts 39.7 percent Formaldehyde solution and 40 parts of 38.75 percent sodium bisulfite solution are formed, heated on the steam bath until solution occurs. After adding methyl alcohol After filtering the ether, the new body precipitates as an almost white powder can be dissolved from alcohol ether.

3. 2 - n - Propylhexahydropyridinmethansulfonsaures Natrium. 2,54 Teile 2-n-Propylhexahydropyridin (Coniin) werden mit einer Formaldehydbisulfitlösung aus 5,37 Teilen 38,75prozentiger Natriumbisulfitlösung und 1,51 Teilen 39,68prozentiger Formaldehydlösung nach Beispiel 2 verarbeitet. Das Kondensationsprodukt kristallisiert aus wenig Methylalkohol und ist in Wasser leicht löslich.3. Sodium 2-n-propylhexahydropyridine methanesulfonic acid. 2.54 Parts of 2-n-propylhexahydropyridine (Coniin) are mixed with a formaldehyde bisulfite solution from 5.37 parts of 38.75 percent sodium bisulfite solution and 1.51 parts of 39.68 percent Formaldehyde solution processed according to Example 2. The condensation product crystallizes from a little methyl alcohol and is easily soluble in water.

4. Chinatoxinmethansulfonsaures Natrium. Die Darstellung erfolgt analog Beispiel e aus 25 Teilen Chinatoxin, 6 Teilen 39,7prozentiger Formaldehydlösung und 21 Teilen 38,75-prozentiger Natriumbisulfitlösung. Das Kondensationsprodukt läßt sich aus Alkoholäther umlösen.4. Sodium quinatoxine methanesulfonic acid. The display is analogous Example e from 25 parts of quinatoxine, 6 parts of 39.7 percent formaldehyde solution and 21 parts of 38.75 percent sodium bisulfite solution. The condensation product can be dissolved from alcohol ether.

Claims (1)

PATENT-ANSPRIICH-Abänderung des durch', Patent q.2-1505 geschützten Verfahrens zur Darstellung von N-methylschwefligsauren Salzen sekundärer aromatisch-aliphatischer Amine, dadurch gekennzeichnet, das man hier Formaldehydbisulfit auf sekundäre Amine mit zyklisch gebundenem Stickstoffatom zur Einwirkung bringt.PATENT CLAIM modification of that protected by ', patent q.2-1505 Process for the preparation of N-methylsulfuric acid salts of secondary aromatic-aliphatic Amines, characterized in that there is formaldehyde bisulfite on secondary amines with a cyclically bonded nitrogen atom to act.
DEF49555D 1920-06-01 1920-12-17 Process for the preparation of N-methylsulphurous acid salts of secondary amines Expired DE432420C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF49555D DE432420C (en) 1920-06-01 1920-12-17 Process for the preparation of N-methylsulphurous acid salts of secondary amines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF46914D DE421505C (en) 1920-06-01 1920-06-01 Process for the preparation of N-methylsulfurous acid salts of secondary aromatic-aliphatic amines
DEF49555D DE432420C (en) 1920-06-01 1920-12-17 Process for the preparation of N-methylsulphurous acid salts of secondary amines

Publications (1)

Publication Number Publication Date
DE432420C true DE432420C (en) 1926-08-13

Family

ID=32909353

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF49555D Expired DE432420C (en) 1920-06-01 1920-12-17 Process for the preparation of N-methylsulphurous acid salts of secondary amines

Country Status (1)

Country Link
DE (1) DE432420C (en)

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