CH311607A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number
CH311607A
CH311607A CH311607DA CH311607A CH 311607 A CH311607 A CH 311607A CH 311607D A CH311607D A CH 311607DA CH 311607 A CH311607 A CH 311607A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
benzyl
butyl
chloro
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag 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
Application filed by Cilag Ag filed Critical Cilag Ag
Publication of CH311607A publication Critical patent/CH311607A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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 substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14Heterocyclic 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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäure-     (2-halogen-6-methyl-anilids).



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten FettsÏure-(2-halogen-6  methyl-anilids), welehes    dadurch   gekennzeich-    net ist, dass man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich a. bspaltenden Rest bedeutet, mit N-Benzyl-N-n-butyl-amin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austausch gegen den basisehen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy- oder   Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den Benzyl-butyl-aminrest erfolgt z.   B.    durch einfaches Erwärmen mit   N-Benzyl-N-bllt-yl-amin    gegebenenfalls in Gegenwart eines basisch re  agierenden Kondensationsmittels    oder von   N-    Benzyl-N-butyl-amin im ¯berschu¯. Das N   Benzyl-N-butyl-aminoaeet- (2-chlor-6-methyl-    anilid) ist ein farbloses, unter 0, 1 mm Hg bei 180¯ siedendes Íl, das naeli einiger Zeit zu farblosen, bei   33     schmelzenden Kristallen erstarrt. Das Hydrochlorid der Base sehmilzt bei 182-184¯.



   Das   neuve    Anilid soll   als Lokalanästhetikum    und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel:
100. Gewichtsteile Chloracet- (2-chlor-6-methyl-anilid) (gewonnen durch Umsetzen von   2-Chlor-6-methyl-anilin    mit Chloracetylchlorid in Gegenwart von   Natriumaceta. t, Schmp.    140 bis   141 )    werden in 500 Gewichtsteilen Benzol suspendiert und mit 157 Gewichtsteilen N Benzyl-N-butyl-amin versetzt. Die Temperatur steigt dabei leieht an, und ein grosser Teil des   Beaktionsgemisches    geht in   Losung.    Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei Siedetemperatur. Anschliessend wird mit Wasser versetzt, mit Natronlauge alkalisch gemacht und das sieh   abseheidende    Öl in Äther aufgenommen.

   Nach dem Trocknen der   ätheri-    schen   Losung    und Verjagen des   Losungsmit-    tels verbleibt ein   Ö1,    das durch   Vakuumdestil-    lation gereinigt wird. Man   erhält 1t 7    Ge  wiehtsteile    reines   N-Benzyl-N-butyl-aminoacet-     (2-chlor-6-methyl-anilid), was einer Ausbeute e von   57 /o entsprieht.     



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6  methyl-anilids),    dadurch gekennzeichnet, dass ¯ man eine Verbindung der Formel 

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





  



  Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).



   The subject of the present patent forms a process for the production of a new basic substituted FettsÏure- (2-halo-6-methyl-anilids), which is characterized by the fact that a compound of the formula
EMI1.1
 in which X is a reactive, during the reaction a. The splitting radical means reacted with N-benzyl-N-n-butyl-amine.



   The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the benzyl-butyl-amine residue takes place z. B. by simply heating with N-benzyl-N-bllt-yl-amine optionally in the presence of a basic re acting condensing agent or N-benzyl-N-butyl-amine in excess. The N benzyl-N-butyl-aminoaeet- (2-chloro-6-methyl-anilide) is a colorless oil, boiling below 0.1 mm Hg at 180¯, which after a while solidifies to colorless crystals which melt at 33. The base hydrochloride melts at 182-184¯.



   The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives.



   Example:
100 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are dissolved in 500 parts by weight of benzene suspended and treated with 157 parts by weight of N benzyl-N-butyl-amine. The temperature rises, and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at boiling temperature. Then water is added, the mixture is made alkaline with sodium hydroxide solution and the oil which separates out is taken up in ether.

   After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 1t 7 parts by weight of pure N-benzyl-N-butyl-aminoacet- (2-chloro-6-methyl-anilide) are obtained, which corresponds to a yield e of 57%.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is a compound of the formula

** 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 basisch substituierten Fettsäure- (2-halogen-6-methyl-anilids). Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten FettsÏure-(2-halogen-6 methyl-anilids), welehes dadurch gekennzeich- net ist, dass man eine Verbindung der Formel EMI1.1 in welcher X einen reaktionsfähigen, während der Reaktion sich a. bspaltenden Rest bedeutet, mit N-Benzyl-N-n-butyl-amin umsetzt. The subject of the present patent forms a process for the production of a new basic substituted FettsÏure- (2-halo-6-methyl-anilids), which is characterized by the fact that a compound of the formula EMI1.1 in which X is a reactive, during the reaction a. The cleaving radical means reacted with N-benzyl-N-n-butyl-amine. Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austausch gegen den basisehen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Benzyl-butyl-aminrest erfolgt z. B. durch einfaches Erwärmen mit N-Benzyl-N-bllt-yl-amin gegebenenfalls in Gegenwart eines basisch re agierenden Kondensationsmittels oder von N- Benzyl-N-butyl-amin im ¯berschu¯. Das N Benzyl-N-butyl-aminoaeet- (2-chlor-6-methyl- anilid) ist ein farbloses, unter 0, 1 mm Hg bei 180¯ siedendes Íl, das naeli einiger Zeit zu farblosen, bei 33 schmelzenden Kristallen erstarrt. Das Hydrochlorid der Base sehmilzt bei 182-184¯. The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the benzyl-butyl-amine residue takes place z. B. by simply heating with N-benzyl-N-bllt-yl-amine optionally in the presence of a basic re acting condensing agent or N-benzyl-N-butyl-amine in excess. The N benzyl-N-butyl-aminoaeet- (2-chloro-6-methyl-anilide) is a colorless oil, boiling below 0.1 mm Hg at 180¯, which after a while solidifies to colorless crystals which melt at 33. The base hydrochloride melts at 182-184¯. Das neuve Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden. The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives. Beispiel: 100. Gewichtsteile Chloracet- (2-chlor-6-methyl-anilid) (gewonnen durch Umsetzen von 2-Chlor-6-methyl-anilin mit Chloracetylchlorid in Gegenwart von Natriumaceta. t, Schmp. 140 bis 141 ) werden in 500 Gewichtsteilen Benzol suspendiert und mit 157 Gewichtsteilen N Benzyl-N-butyl-amin versetzt. Die Temperatur steigt dabei leieht an, und ein grosser Teil des Beaktionsgemisches geht in Losung. Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei Siedetemperatur. Anschliessend wird mit Wasser versetzt, mit Natronlauge alkalisch gemacht und das sieh abseheidende Öl in Äther aufgenommen. Example: 100 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are dissolved in 500 parts by weight of benzene suspended and treated with 157 parts by weight of N benzyl-N-butyl-amine. The temperature rises and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at boiling temperature. Then water is added, the mixture is made alkaline with sodium hydroxide solution and the oil which separates out is taken up in ether. Nach dem Trocknen der ätheri- schen Losung und Verjagen des Losungsmit- tels verbleibt ein Ö1, das durch Vakuumdestil- lation gereinigt wird. Man erhält 1t 7 Ge wiehtsteile reines N-Benzyl-N-butyl-aminoacet- (2-chlor-6-methyl-anilid), was einer Ausbeute e von 57 /o entsprieht. After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 1t 7 parts by weight of pure N-benzyl-N-butyl-aminoacet- (2-chloro-6-methyl-anilide) are obtained, which corresponds to a yield e of 57%. PATENTANSPRUCH : Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6 methyl-anilids), dadurch gekennzeichnet, dass ¯ man eine Verbindung der Formel EMI2.1 in weleher X einen reaktionsfÏhigen, wÏhrend der Reaktion sich abspaltenden Rest bedeutet, mit N-Benzyl-N-butyl-amin umsetzt. Das auf diese Weise erhaltene N-Benzyl-N-butyl-amino- acet-(2-chlor-6-methyl-anilid) bildet ein farbloses, unter 0, 1 mm Hg bei 180 siedendes öl, das nach einiger Zeit zu farblosen, bei 33" schmelzenden Kristallen erstarrt. Das Hydrochlorid der Base schmilzt bei 182-184¯. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is a compound of the formula EMI2.1 in which X is a reactive residue that is split off during the reaction, reacts with N-benzyl-N-butyl-amine. The N-benzyl-N-butyl-amino-acet- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless oil boiling below 0.1 mm Hg at 180, which after some time becomes colorless, solidified at 33 "melting crystals. The hydrochloride of the base melts at 182-184¯. Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. The new anilide will be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH : Verfahren nach Patentansprueh, dadureh gekennzeichnet, dass man ein Halogenaeet-(2- chlor-6-methyl-anilid) mit N-Benzyl-N-butyl- amin reagieren lässt. SUBClaim: Process according to patent claim, characterized in that a halogenate (2-chloro-6-methyl-anilide) is allowed to react with N-benzyl-N-butylamine.
CH311607D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311607A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311607T 1952-02-25
CH307799T 1952-11-25

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CH311607A true CH311607A (en) 1955-11-30

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Cited By (8)

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Publication number Priority date Publication date Assignee Title
US10780083B1 (en) 2019-03-11 2020-09-22 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10786485B1 (en) 2019-03-11 2020-09-29 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10842798B1 (en) 2019-11-06 2020-11-24 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10927096B2 (en) 2019-03-11 2021-02-23 Nocion Therapeutics, Inc. Ester substituted ion channel blockers and methods for use
US10934263B2 (en) 2019-03-11 2021-03-02 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10933055B1 (en) 2019-11-06 2021-03-02 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10968179B2 (en) 2019-03-11 2021-04-06 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11332446B2 (en) 2020-03-11 2022-05-17 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11512058B2 (en) 2019-03-11 2022-11-29 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10786485B1 (en) 2019-03-11 2020-09-29 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10828287B2 (en) 2019-03-11 2020-11-10 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10780083B1 (en) 2019-03-11 2020-09-22 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10927096B2 (en) 2019-03-11 2021-02-23 Nocion Therapeutics, Inc. Ester substituted ion channel blockers and methods for use
US10934263B2 (en) 2019-03-11 2021-03-02 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11643404B2 (en) 2019-03-11 2023-05-09 Nocion Therapeutics, Inc. Ester substituted ion channel blockers and methods for use
US10968179B2 (en) 2019-03-11 2021-04-06 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11603355B2 (en) 2019-03-11 2023-03-14 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11377422B2 (en) 2019-03-11 2022-07-05 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10842798B1 (en) 2019-11-06 2020-11-24 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US10933055B1 (en) 2019-11-06 2021-03-02 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11696912B2 (en) 2019-11-06 2023-07-11 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
US11332446B2 (en) 2020-03-11 2022-05-17 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use

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