CH311606A - 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
- CH311606A CH311606A CH311606DA CH311606A CH 311606 A CH311606 A CH 311606A CH 311606D A CH311606D A CH 311606DA CH 311606 A CH311606 A CH 311606A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- butyl
- chloro
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000003589 local anesthetic agent Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
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 bil (let ein Verfahren zur Herstellung eines neuen basiseli substituierten Fettsäure- (2-halogen-6- methyl-anilids), welches dadurch gekennzeich- net ist, dass man eine Verbindung der Formel
EMI1.1
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Di-n-butyl-amin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. e-iner Alkylsulfo- nyloxy-oder Arylsulfonyloxygruppe, bestehen.
Der Austausch der Gruppe X gegen den Di n-butyl-aminrest erfolgt z. B. durch einfaches Erwärmen mit Di-n-butyl-amin gegebenen- falls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von Di-n-butyl- amin im Überschu#. Das Di-n-butyl-aminoacet- (2-ehlor-6-methyl-anilid) ist ein farbloses, unter 0, 06 mm Hg bei 145 siedendes Öl. Das Hydroehlorid der Base schmilzt bei 145 bis 1470.
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel :
31 Gewichtsteile Chloracet- (2-chlor-6-me- thyl-a. nilid) (gewonnen durch Umsetzen von 2 Chlor-6-methyl-anüin mit Chloracetylchlorid in Gegenwart von Natriumacetat, Schmp. 140 bis 141 ) werden in 80 Gewichtsteilen Äthanol suspendiert und mit. 55 Gewichtsteilen Di-n butyl-amin versetzt. Die Temperatur steigt dabei leicht an und ein grosser Teil des Reak tionsgemisches geht in Losung. Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei 65-75 .
Eine Probe mit Wasser und nachfolgend mit verdünnter Salzsäure versetzt ergibt wieder Lösung des ausgefallenen Niederschlages. Mit Wasserdampf wird hierauf der Alkohol und das übersehüssige Di-n-butyl-amin abgeblasen und nach dem Erkalten das zurückbleibende Öl in Äther aufgenommen. Naeh dem Trocknen der ätherischen Losung und Verjagen des Losungsmittels verbleibt ein 01, das durch Vakuumdestillation gereinigt wird. Man erhält 43 Gewichtsteile reines Di-n-butyl-aminoacet- (2-chlor-6-methyl-anilid). Die Umsetzung mit Di-n-butyl-amin kann aneh in Benzol stattfinden.
PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6methyl-anilids), dadureh 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 bil (let a process for the production of a new basiseli substituted fatty acid (2-halogen-6-methyl-anilide), which is characterized in that a compound of the formula
EMI1.1
in which X is a reactive radical which is split off during the reaction, is reacted with di-n-butylamine.
The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. e-iner alkylsulfonyloxy or arylsulfonyloxy group exist.
The exchange of the group X against the di n-butyl-amine residue takes place, for. B. by simply heating with di-n-butyl-amine, if necessary in the presence of a basic condensing agent or an excess of di-n-butyl-amine. Di-n-butyl-aminoacet- (2-chloro-6-methyl-anilide) is a colorless oil boiling below 0.06 mm Hg at 145. The hydrochloride of the base melts at 145 to 1470.
The new anilide is to be used as a local anesthetic and as an intermediate product for the production of further derivatives.
Example:
31 parts by weight of chloroacet- (2-chloro-6-methyl-a. Nilide) (obtained by reacting 2 chloro-6-methyl-anuine with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are in 80 parts by weight of ethanol suspended and with. 55 parts by weight of di-n-butylamine are added. The temperature rises slightly 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 65-75.
A sample with water and then mixed with dilute hydrochloric acid results in a solution of the precipitate. The alcohol and the excess di-n-butyl-amine are then blown off with steam and, after cooling, the remaining oil is absorbed in ether. After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 43 parts by weight of pure di-n-butyl-aminoacet- (2-chloro-6-methyl-anilide) are obtained. The reaction with di-n-butylamine can also take place in benzene.
PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halo-6methyl-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 |
|---|---|---|---|
| CH311606T | 1952-02-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311606A true CH311606A (en) | 1955-11-30 |
Family
ID=25735339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311606D CH311606A (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) | CH311606A (en) |
Cited By (9)
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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 |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged 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 |
| 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 |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
-
1952
- 1952-02-25 CH CH311606D patent/CH311606A/en unknown
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11643404B2 (en) | 2019-03-11 | 2023-05-09 | Nocion Therapeutics, Inc. | Ester substituted 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 |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12195428B2 (en) | 2019-03-11 | 2025-01-14 | 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 |
| US11512058B2 (en) | 2019-03-11 | 2022-11-29 | Nocion Therapeutics, Inc. | Charged 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 |
| US10968179B2 (en) | 2019-03-11 | 2021-04-06 | 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 |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | 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 |
| 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 |
| US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12303496B2 (en) | 2019-11-06 | 2025-05-20 | 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 |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
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