CH412891A - Process for the preparation of a new hydrazine derivative - Google Patents

Process for the preparation of a new hydrazine derivative

Info

Publication number
CH412891A
CH412891A CH1518564A CH1518564A CH412891A CH 412891 A CH412891 A CH 412891A CH 1518564 A CH1518564 A CH 1518564A CH 1518564 A CH1518564 A CH 1518564A CH 412891 A CH412891 A CH 412891A
Authority
CH
Switzerland
Prior art keywords
sulfamyl
dimethyl
piperidyl
chloro
preparation
Prior art date
Application number
CH1518564A
Other languages
German (de)
Inventor
Ernst Dr Jucker
Adolf Dr Lindenmann
Original Assignee
Sandoz 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 to NL123596D priority Critical patent/NL123596C/xx
Priority claimed from CH1254760A external-priority patent/CH396905A/en
Application filed by Sandoz Ag filed Critical Sandoz Ag
Priority to CH1518564A priority patent/CH412891A/en
Priority claimed from CH654761A external-priority patent/CH418335A/en
Publication of CH412891A publication Critical patent/CH412891A/en

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
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

  



  Verfahren zur Herstellung eines neuen   Hydrazin-Derivates   
Es wurde gefunden, dass man zum bisher unbekannten   N- [2', 6'-Dimethyl-piperidyl- (l')]-3-sulfamyl-      4-chlor-benzoesäureamid    der Formel I
EMI1.1     
 gelangt, indem man 3-Sulfamyl-4-chlor-benzoylchlorid mit   l-Amino-2,    6-dimethyl-piperidin umsetzt.



   Beispiel
N-[2',6'-Dimethyl-piperidyl-(1')]   3-sulfamyl-4-chlor-benzoesiiureamid   
Eine Lösung von 3, 8 g   1-Amino-2, 6-dimethyl-    piperidin und 3, 0 g TriÏthylamin in   150    ccm Chloroform wird unter Rühren bei 20-25¯ innert 20 Min. mit 7, 6 g 3-Sulfamyl-4-chlor-benzoylchlorid versetzt und die gelbe Reaktionslösung anschliessend 48 Std. bei Zimmertemperatur weitergerührt. Darauf wird im Vakuum zur Trockne abgedampft, der Rückstand in 200 ccm Essigsäureäthylester aufgenommen und mit total 200 ccm Wasser gewaschen.

   Nach Trocknen  über Magnesiumsulfat wird der Essigsäureäthylester im Vakuum abdestilliert und derRückstand über Alu    miniumoxyd    chromatographiert, wobei das   N- [2',    6'   Dimethyl-piperidyl- (1')]-3-sulfamyl-4-chlor-benzo-    säureamid mit einem Losungsmittelgemisch   Chloro-    form/Methanol (9 : 1) eluiert wird. Nach Umkristalli    sieren    aus Methanol/Diisopropyläther schmilzt das   Hydrazin-Derivat bei 233-235 .     



   PATENTANSPRUCH
Verfahren zur Herstellung des bisher unbekann    ten    N- [2',   6'-Dimethyl-piperidyl-    (1')]-3-sulfamyl-4 chlor-benzoesÏureamids der Formel   I,   
EMI1.2     
 dadurch gekennzeichnet, dass man 3-Sulfamyl-4chlor-benzoylchlorid mit 1-Amino-2,6-dimethyl-piperidin umsetzt. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the preparation of a new hydrazine derivative
It has been found that the previously unknown N- [2 ', 6'-dimethyl-piperidyl- (1')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I
EMI1.1
 obtained by reacting 3-sulfamyl-4-chlorobenzoyl chloride with l-amino-2,6-dimethyl-piperidine.



   example
N- [2 ', 6'-Dimethyl-piperidyl- (1')] 3-sulfamyl-4-chloro-benzoic acid amide
A solution of 3.8 g of 1-amino-2,6-dimethylpiperidine and 3.0 g of triethylamine in 150 cc of chloroform is mixed with 7.6 g of 3-sulfamyl-4 within 20 minutes while stirring at 20-25 ° -chlorobenzoyl chloride is added and the yellow reaction solution is then stirred for a further 48 hours at room temperature. It is then evaporated to dryness in vacuo, the residue is taken up in 200 cc of ethyl acetate and washed with a total of 200 cc of water.

   After drying over magnesium sulfate, the ethyl acetate is distilled off in vacuo and the residue is chromatographed over aluminum oxide, the N- [2 ', 6' dimethyl-piperidyl- (1 ')] - 3-sulfamyl-4-chlorobenzoic acid amide with a Solvent mixture chloroform / methanol (9: 1) is eluted. After recrystallization from methanol / diisopropyl ether, the hydrazine derivative melts at 233-235.



   PATENT CLAIM
Process for the preparation of the previously unknown N- [2 ', 6'-dimethyl-piperidyl- (1')] - 3-sulfamyl-4 chloro-benzoesÏureamids of the formula I,
EMI1.2
 characterized in that 3-sulfamyl-4-chlorobenzoyl chloride is reacted with 1-amino-2,6-dimethyl-piperidine.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines neuen Hydrazin-Derivates Es wurde gefunden, dass man zum bisher unbekannten N- [2', 6'-Dimethyl-piperidyl- (l')]-3-sulfamyl- 4-chlor-benzoesäureamid der Formel I EMI1.1 gelangt, indem man 3-Sulfamyl-4-chlor-benzoylchlorid mit l-Amino-2, 6-dimethyl-piperidin umsetzt. Process for the preparation of a new hydrazine derivative It has been found that the previously unknown N- [2 ', 6'-dimethyl-piperidyl- (1')] -3-sulfamyl-4-chloro-benzoic acid amide of the formula I EMI1.1 obtained by reacting 3-sulfamyl-4-chlorobenzoyl chloride with l-amino-2,6-dimethyl-piperidine. Beispiel N-[2',6'-Dimethyl-piperidyl-(1')] 3-sulfamyl-4-chlor-benzoesiiureamid Eine Lösung von 3, 8 g 1-Amino-2, 6-dimethyl- piperidin und 3, 0 g TriÏthylamin in 150 ccm Chloroform wird unter Rühren bei 20-25¯ innert 20 Min. mit 7, 6 g 3-Sulfamyl-4-chlor-benzoylchlorid versetzt und die gelbe Reaktionslösung anschliessend 48 Std. bei Zimmertemperatur weitergerührt. Darauf wird im Vakuum zur Trockne abgedampft, der Rückstand in 200 ccm Essigsäureäthylester aufgenommen und mit total 200 ccm Wasser gewaschen. example N- [2 ', 6'-Dimethyl-piperidyl- (1')] 3-sulfamyl-4-chloro-benzoic acid amide A solution of 3.8 g of 1-amino-2,6-dimethylpiperidine and 3.0 g of triethylamine in 150 cc of chloroform is mixed with 7.6 g of 3-sulfamyl-4 within 20 minutes while stirring at 20-25 ° -chlorobenzoyl chloride is added and the yellow reaction solution is then stirred for a further 48 hours at room temperature. It is then evaporated to dryness in vacuo, the residue is taken up in 200 cc of ethyl acetate and washed with a total of 200 cc of water. Nach Trocknen über Magnesiumsulfat wird der Essigsäureäthylester im Vakuum abdestilliert und derRückstand über Alu miniumoxyd chromatographiert, wobei das N- [2', 6' Dimethyl-piperidyl- (1')]-3-sulfamyl-4-chlor-benzo- säureamid mit einem Losungsmittelgemisch Chloro- form/Methanol (9 : 1) eluiert wird. Nach Umkristalli sieren aus Methanol/Diisopropyläther schmilzt das Hydrazin-Derivat bei 233-235 . After drying over magnesium sulfate, the ethyl acetate is distilled off in vacuo and the residue is chromatographed over aluminum oxide, the N- [2 ', 6' dimethyl-piperidyl- (1 ')] - 3-sulfamyl-4-chlorobenzoic acid amide with a Solvent mixture chloroform / methanol (9: 1) is eluted. After recrystallization from methanol / diisopropyl ether, the hydrazine derivative melts at 233-235. PATENTANSPRUCH Verfahren zur Herstellung des bisher unbekann ten N- [2', 6'-Dimethyl-piperidyl- (1')]-3-sulfamyl-4 chlor-benzoesÏureamids der Formel I, EMI1.2 dadurch gekennzeichnet, dass man 3-Sulfamyl-4chlor-benzoylchlorid mit 1-Amino-2,6-dimethyl-piperidin umsetzt. PATENT CLAIM Process for the preparation of the previously unknown N- [2 ', 6'-dimethyl-piperidyl- (1')] - 3-sulfamyl-4 chloro-benzoesÏureamids of the formula I, EMI1.2 characterized in that 3-sulfamyl-4-chlorobenzoyl chloride is reacted with 1-amino-2,6-dimethyl-piperidine.
CH1518564A 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative CH412891A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
NL123596D NL123596C (en) 1960-11-09
CH1518564A CH412891A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH1254760A CH396905A (en) 1960-11-09 1960-11-09 Process for the preparation of new hydrazine derivatives
CH1354460 1960-12-02
CH1518564A CH412891A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative
CH654761A CH418335A (en) 1960-11-09 1961-06-06 Process for the preparation of new hydrazine derivatives
CH1047461 1961-09-11
CH1518864A CH412892A (en) 1960-11-09 1961-09-11 Process for the preparation of new hydrazine derivatives

Publications (1)

Publication Number Publication Date
CH412891A true CH412891A (en) 1966-05-15

Family

ID=27561117

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1518564A CH412891A (en) 1960-11-09 1961-06-06 Process for the preparation of a new hydrazine derivative

Country Status (2)

Country Link
CH (1) CH412891A (en)
NL (1) NL123596C (en)

Also Published As

Publication number Publication date
NL123596C (en)

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