CH240135A - Process for the preparation of a basic aralkyl ether. - Google Patents
Process for the preparation of a basic aralkyl ether.Info
- Publication number
- CH240135A CH240135A CH240135DA CH240135A CH 240135 A CH240135 A CH 240135A CH 240135D A CH240135D A CH 240135DA CH 240135 A CH240135 A CH 240135A
- Authority
- CH
- Switzerland
- Prior art keywords
- basic
- preparation
- ether
- parts
- aralkyl ether
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 5
- -1 aralkyl ether Chemical compound 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229940072033 potash Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QDYKZBKCLHBUHU-UHFFFAOYSA-N cyclohexyl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1 QDYKZBKCLHBUHU-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- TYUZUALRVQGHQA-UHFFFAOYSA-N [chloro(cyclohexyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1CCCCC1 TYUZUALRVQGHQA-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung eines basischen Aralkyläthers. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines basischen Aralkyläthers aus a-Cyclohexyl- benzylalkohol und Diäthylaminoäthanol. Das Verfahren ist dadurch gekennzeichnet, dass ein reaktionsfähiger Ester des einen Alkohols mit einem Alkoholat des andern Alkohols umgesetzt wird.
Der erhaltene a-Cyclohexyl- benzyl - (diäthylaminoäthyl) - äther ist eine Flüssigkeit vom gp. ",ss 130-132 ; er soll therapeutische Verwendung finden.
<I>Beispiel:</I> Zu einer Suspension von 20 Teilen pulveri siertem Natriumamid in 300 Teilen absol. Benzol werden 95 Teile Cyclohexyl-phenyl- carbinol zugetropft und 1 Stunde bei 60 ge rührt. Dann werden 70 Teile ss-Chloräthyl- diäthylamin zugegeben und das Ganze 6 Stun den unter Rückfluss und Rühren erhitzt. Nach dem Abkühlen wird mit Wasser versetzt und mit 10%iger Salzsäure mehrmals aus geschüttelt.
Die vereinigten salzsauren Aus- züge werden mit Pottasche alkalisch gemacht, die ausgeschiedene Base in Äther aufgenom men, die Ätherlösung mit konz. Pottasche lösung gewaschen, über fester Pottasche ge trocknet und der Äther abgedampft. Der Rückstand siedet bei 0,6 mm bei 130-1ä2 . Ausbeute 95 Teile.
Dieselbe Verbindung kann auch auf fol gende Weise erhalten werden: In einer Lö sung von 11 Teilen Diäthylaminoäthanol in 40 Teilen Benzol werden 2 Teile Natrium auf gelöst. Nach dem Erkalten wird die berech nete Menge a-Cyclohexyl-benzylchlorid in Portionen zugegeben. Nach Abklingen der Reaktion wird noch eine Stunde lang am Rückflusskühler auf dem Wasserbad erhitzt, alsdann gekühlt, mit Wasser ausgeschüttelt und schliesslich unter Kühlung mit verdünn ter Salzsäure verrührt. Nach nochmaligem Waschen des Benzols mit Wasser werden die vereinigten Auszüge mit Pottasche gefällt und die abgeschiedene Base in Äther auf genommen. Nach Entfernen des Lösungs- mittels destilliert die Base bei 130-13?' und 0,6 mm.
Der neue Äther soll therapeutisehe Verwendung finden.
Process for the preparation of a basic aralkyl ether. Subject of the present Zusatzpaten tes is a method for the preparation of a basic aralkyl ether from α-cyclohexyl benzyl alcohol and diethylaminoethanol. The method is characterized in that a reactive ester of one alcohol is reacted with an alcoholate of the other alcohol.
The obtained a-cyclohexylbenzyl - (diethylaminoethyl) - ether is a liquid of gp. ", pp. 130-132; it should find therapeutic use.
<I> Example: </I> To a suspension of 20 parts of powdered sodium amide in 300 parts of absol. Benzene, 95 parts of cyclohexyl-phenyl-carbinol are added dropwise and the mixture is stirred at 60 for 1 hour. Then 70 parts of β-chloroethyl diethylamine are added and the whole thing is heated under reflux and stirring for 6 hours. After cooling, water is added and the mixture is shaken out several times with 10% hydrochloric acid.
The combined hydrochloric acid extracts are made alkaline with potash, the precipitated base is taken up in ether, the ethereal solution with conc. Washed potash solution, dried over solid potash and evaporated the ether. The residue boils at 0.6 mm at 130-1-2. Yield 95 parts.
The same compound can also be obtained in the following manner: 2 parts of sodium are dissolved in a solution of 11 parts of diethylaminoethanol in 40 parts of benzene. After cooling, the calculated amount of α-cyclohexylbenzyl chloride is added in portions. After the reaction has subsided, the mixture is heated in the reflux condenser on the water bath for a further hour, then cooled, extracted with water and finally stirred with dilute hydrochloric acid while cooling. After washing the benzene again with water, the combined extracts are precipitated with potash and the base which has separated out is taken up in ether. After removing the solvent, the base distills at 130-13? ' and 0.6 mm.
The new ether should be used in therapy.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240135T | 1942-09-23 | ||
| CH2397799X | 1942-09-23 | ||
| GB15558/43A GB585994A (en) | 1943-09-22 | 1943-09-22 | Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240135A true CH240135A (en) | 1945-11-30 |
Family
ID=32110426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240135D CH240135A (en) | 1942-09-23 | 1942-09-23 | Process for the preparation of a basic aralkyl ether. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240135A (en) |
-
1942
- 1942-09-23 CH CH240135D patent/CH240135A/en unknown
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