CH327986A - Process for the production of new basic esters - Google Patents
Process for the production of new basic estersInfo
- Publication number
- CH327986A CH327986A CH327986DA CH327986A CH 327986 A CH327986 A CH 327986A CH 327986D A CH327986D A CH 327986DA CH 327986 A CH327986 A CH 327986A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- new basic
- production
- ester
- basic esters
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- VKKTUDKKYOOLGG-UHFFFAOYSA-N 1-(diethylamino)propan-1-ol Chemical compound CCC(O)N(CC)CC VKKTUDKKYOOLGG-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 1
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 1
- 101100241859 Mus musculus Oacyl gene Proteins 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung neuer basischer Ester
Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung von neuen basischen Estern. Es ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.1
in welcher R1 Methyl oder Äthyl und R2 Äthyl, Propyl oder Butyl bedeuten, mit einer Verbindung der Formel
EMI1.2
umsetzt, in welcher R3 einen niederen Alkyl- rest, n die Zahl 2 oder 3 und in beiden Formeln Z und V sich mit Ausnahme eines in einem von ihnen enthaltenen Sauerstoffatoms bei der Reaktion abspaltende Reste bedeuten.
Die neuen Ester stellen wertvolle Spasmo- lytika und Anticholinergika dar und weisen ferner auch eine sehr gute zentralanalgetische und starke lokalanästhetische Wirkung auf.
Durch Umwandlung der Ester in quater näre Ammoniumverbindungen gelangt man zu weiteren Substanzen mit guten krampflosen- den Eigenschaften und besonders ausgepräg- ter anticholinergischer Wirkung.
Man kann beispielsweise so vorgehen, dal man eine Säure der Formel I (Z = OH) mit einem basischen Alkohol der Formel II (V = OH) in Gegenwart eines Veresternngs- katalysators umsetzt, oder dass man einen niederen Alkylester (Z = OAlkyl), ein Anhydrid, z. B. das reine Anhydrid (Z = OAcyl) oder ein gemischtes Anhydrid, mit einem Alkohol der Formel II oder einem Salz desselben, gegebenenfalls in Gegenwart von basisch reagierenden Kondensationsmitteln, umsetzt.
Ferner kann man auch eine Säure der Formel I oder ein Salz derselben (Z = OH bzw. OMe) mit einem reaktionsfähigen Ester eines Alkohols der Formel II, z. B. einem IIalogenwasserstoffester (V = Hal), oder einem Salz eines solchen umsetzen.
Beispiel 1
9 g 2-Oxy-2-phenyl-3-methyl-pentansaure- (: 1.) werden in 100 cm3 Isopropanol mit 6, 8 g Diäthylamino-äthylchlorid 2 Stunden zum Sieden erhitzt. Das Hydrochlorid des gebildeten Esters kristallisiert beim Erkalten aus.
Nach einigen Stunden wird es abgesaugt und aus Isopropanol umkristallisiert. Man erhält so 12, 2 g, d. s. 810/o d. Th., an Hydrocldorid, das bei 167-168 C schmilzt. Aus diesem kann der freie basische Ester mit Hilfe von Natriumcarbonatlösung hergestellt werden. Dieser stellt ein farbloses, säurelösliches öl dar.
Beispiel 2
Den in Beispiel 1 beschriebenen Ester erhält man auch, wenn man 1 Mol 2-Oxy-2- phenyl-3-methyl-pentansÏure-(1)-methylester mit einem Überschuss Diäthylamino-äthanol in Gegenwart von wenig Natriummethylat auf 170-180 C erhitzt. Die Aufarbeitung erfolgt, nach Entfernmng des überschüssigen Diäthylamino-äthanols im Vakuum, wie in Beispiel 1 beschrieben.
Beispiel 3
9 g 2-Oxy-2-phenyl-3-methyl-pentansaure- (1) und 7, 5 g 3-Diäthylamino-propylchlorid werden in 100 cm3 Isopropanol 2 Stunden zum Sieden erhitzt. Das Hydrochlorid des gebildeten Esters kristallisiert beim Erkalten aus.
Nach einigen Stunden wird es abgesaugt und aus Isopropanol umkristallisiert. Man erhält so 13 g an Hydrochlorid, das bei 116-117 C sehmilzt. Aus diesem kann der freie Ester mit Hilfe von Natriumcarbonatlosung hergestellt werden. Dieser stellt ein farbloses, säure- lösliehes öl dar.
Beispiel 4
Der in Beispiel 3 beschriebene Ester kann auch erhalten werden durch Erhitzen von 2-Oxy-2-phenyl-3-methyl-pentansäure- (1)methylester mit einem Überschuss von 3-Di äthylamino-propanol in Gegenwart von wenig Natriummethylat auf 170-180 C. Die Auf arbeitung erfolgt, nach Entfernung des über schüssigen Diäthylamino-propanols im Va kuum, wie in Beispiel 3 beschrieben.
Process for the production of new basic esters
The subject of the present patent is a process for the preparation of new basic esters. It is characterized in that one has a compound of the formula
EMI1.1
in which R1 is methyl or ethyl and R2 is ethyl, propyl or butyl, with a compound of the formula
EMI1.2
in which R3 is a lower alkyl radical, n is the number 2 or 3 and in both formulas Z and V are radicals which are split off during the reaction with the exception of an oxygen atom contained in one of them.
The new esters are valuable spasmolytics and anticholinergics and also have a very good central analgesic and strong local anesthetic effect.
By converting the esters into quaternary ammonium compounds, other substances with good antispasmodic properties and a particularly pronounced anticholinergic effect are obtained.
One can proceed, for example, that an acid of the formula I (Z = OH) is reacted with a basic alcohol of the formula II (V = OH) in the presence of an esterification catalyst, or that a lower alkyl ester (Z = O-alkyl), an anhydride, e.g. B. the pure anhydride (Z = OAcyl) or a mixed anhydride, with an alcohol of the formula II or a salt thereof, optionally in the presence of basic condensing agents, is reacted.
Furthermore, an acid of the formula I or a salt thereof (Z = OH or OMe) can also be used with a reactive ester of an alcohol of the formula II, e.g. B. implement a IIalogenwasserstoffester (V = Hal), or a salt of such.
example 1
9 g of 2-oxy-2-phenyl-3-methyl-pentanoic acid (: 1.) are heated to boiling for 2 hours in 100 cm3 of isopropanol with 6.8 g of diethylaminoethyl chloride. The hydrochloride of the ester formed crystallizes out on cooling.
After a few hours it is filtered off with suction and recrystallized from isopropanol. This gives 12.2 g, i.e. s. 810 / o d. Th., Of hydrochloride, which melts at 167-168 C. The free basic ester can be produced from this with the aid of sodium carbonate solution. This is a colorless, acid-soluble oil.
Example 2
The ester described in Example 1 is also obtained if 1 mol of 2-oxy-2-phenyl-3-methyl-pentanoic acid (1) -methyl ester is heated to 170-180 ° C. with an excess of diethylaminoethanol in the presence of a little sodium methylate . Work-up is carried out as described in Example 1 after the excess diethylaminoethanol has been removed in vacuo.
Example 3
9 g of 2-oxy-2-phenyl-3-methyl-pentanoic acid (1) and 7.5 g of 3-diethylamino-propyl chloride are heated to boiling in 100 cm3 of isopropanol for 2 hours. The hydrochloride of the ester formed crystallizes out on cooling.
After a few hours it is filtered off with suction and recrystallized from isopropanol. 13 g of hydrochloride which melts at 116-117 ° C. are thus obtained. The free ester can be produced from this with the aid of sodium carbonate solution. This is a colorless, acid-soluble oil.
Example 4
The ester described in Example 3 can also be obtained by heating 2-oxy-2-phenyl-3-methyl-pentanoic acid (1) methyl ester with an excess of 3-diethylamino-propanol in the presence of a little sodium methylate to 170-180 C. The work-up is carried out after removal of the excess diethylamino-propanol in a vacuum, as described in Example 3.
Claims (1)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE327986X | 1953-11-24 | ||
| DE200454X | 1954-04-20 | ||
| DE280554X | 1954-05-28 | ||
| DE20654X | 1954-06-02 | ||
| DE200754X | 1954-07-20 | ||
| DE250954X | 1954-09-25 | ||
| CH317305T | 1954-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH327986A true CH327986A (en) | 1958-02-15 |
Family
ID=27561175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH327986D CH327986A (en) | 1953-11-24 | 1954-10-25 | Process for the production of new basic esters |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH327986A (en) |
-
1954
- 1954-10-25 CH CH327986D patent/CH327986A/en unknown
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