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
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
- C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- 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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311607T | 1952-02-25 | ||
CH307799T | 1952-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311607A true CH311607A (en) | 1955-11-30 |
Family
ID=25735340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311607D CH311607A (en) | 1952-02-25 | 1952-02-25 | Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH311607A (en) |
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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 |
-
1952
- 1952-02-25 CH CH311607D patent/CH311607A/en unknown
Cited By (14)
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---|---|---|---|---|
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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