CH154820A - Process for the preparation of 1-dibenzylamino-ethan-2-ol. - Google Patents
Process for the preparation of 1-dibenzylamino-ethan-2-ol.Info
- Publication number
- CH154820A CH154820A CH154820DA CH154820A CH 154820 A CH154820 A CH 154820A CH 154820D A CH154820D A CH 154820DA CH 154820 A CH154820 A CH 154820A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- preparation
- alcohol
- weight
- dibenzylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- WTTWSMJHJFNCQB-UHFFFAOYSA-N 2-(dibenzylamino)ethanol Chemical compound C=1C=CC=CC=1CN(CCO)CC1=CC=CC=C1 WTTWSMJHJFNCQB-UHFFFAOYSA-N 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
- 229940073608 benzyl chloride Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- WBGPDYJIPNTOIB-UHFFFAOYSA-N n,n-dibenzylethanamine Chemical compound C=1C=CC=CC=1CN(CC)CC1=CC=CC=C1 WBGPDYJIPNTOIB-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- -1 arylmethyl halides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung 'von 1-Dibenzylamino-äthan-2-ol. Es wurde gefunden, dass man Alkylol- aminderivate erhalten kann, indem man 1- Aminoalkylo,1e: 2 mit Arylmethylhalogeniden umsetzt, deren Arylrest substituiert sein kann.
Die neuen Verbindungen sind wertvolle Zwischenprodukte für die Herstellung von neuen Verbindungen, besonders für die Her stellung von neuen Heilmitteln und Farb stoffen.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung von 1-Di- benzylamino-äthan-2-ol, welches dadurch ge kennzeichnet ist, dass man Ithanolamin mit Benzylehlorid umsetzt.
Das zur Herstellung von: neuen Heil- mitteln und Farbstoffen verwendbare Ver fahrensprodukt bildet Kristalle vom F. P. 46 bis 47 C; leicht löslich in Äther und Benzol, fast unlöslich in Wasser und um kristallisierbar aus verdünntem Alkohol; das salzsaure Salz kristallisiert aus Alkohol in Blättchen von F. P. 192 C.
<I>Beispiele:</I> 1. 61 Gewichtsteile Äthanolamin und 253 Gewichtsteile Benzylchlorid werden uil- ter Rühren zusammengegeben. Die Tempe ratur des Gemisches steigt bald an; durch passende Kühlung lässt man sie nicht über 90 C kommen. Wenn keine Selbsterwärmung mehr auftritt, werden zwischen 85 und 90 langsam 140 Gewichtsteile pulverisiertes. trockenes Kaliumkarbonat eingetragen; dar auf wird das Gemisch noch zwei Stunden bei Wasserbadtemperatur gerührt.
Alsdann gibt man 500 Teile Wasser zu zur Auflösung des Salzes, lässt abkühlen, trennt das 01 nach Verdünnung mit etwa 200 Teilen Äther von der Salzlösung ab, trocknet über Kalium karbonat und destilliert. Bei 8 mm Druck um 203 oder bei 3 mm Druck um 175 siedet das Produkt als farbloses Öl über, das beim Erkalten vollkommen erstarrt. Aus beute: 220 Gewichtsteile 1-Dibenzylamino- äthanol-2, grosse Kristalle vom F. P. 46 bis 47 C, leicht löslich in Äther und Benzol und fast unlöslich in Wasser, umkristallisier- bar aus verdünntem Alkohol.
Das aus dem 1-Dibenzylaminoäthanol-2 mit Thionylchlo- rid in glatter Umsetzung entstehende salz- saure 1-Dibenzylaminoäthylchlorid kristalli siert aus Alkohol in Blättchen vom F. P. 192 C.
2. 122 Gewichtsteile Athanolamin und 253 Gewichtsteile Benzylchlorid werden zur Reaktion gebracht, das Gemisch wird zwei Stunden auf dem Wasserbade nacherhitzt. Nach dem Abkühlen wird konzentrierte Ka- liumkarbonatlösung und Äther zugesetzt.
Die Ätherlösung wird nach dem Abtrennen und Trocknen über Kaliumkarbonat im Va kuum destilliert und liefert nach einem Vorlauf von etwa 85 Gewichtsteilen Benzyl- chlorid 161 Gewichtsteile bei 3 mm von 170 bis 175 C übergehendes 1-Dibenzylamino- äthanol-2.
Process for the preparation of 1-dibenzylamino-ethan-2-ol. It has been found that alkylolamine derivatives can be obtained by reacting 1-aminoalkylo, 1e: 2 with arylmethyl halides whose aryl radical can be substituted.
The new compounds are valuable intermediates for the production of new compounds, especially for the manufacture of new medicines and dyes.
The present invention relates to a process for the preparation of 1-di-benzylamino-ethan-2-ol, which is characterized in that itethanolamine is reacted with benzyl chloride.
The process product which can be used for the manufacture of: new remedies and dyes forms crystals from F. P. 46 to 47 C; Easily soluble in ether and benzene, almost insoluble in water and can be crystallized from dilute alcohol; the hydrochloric acid salt crystallizes from alcohol in leaves from F. P. 192 C.
<I> Examples: </I> 1. 61 parts by weight of ethanolamine and 253 parts by weight of benzyl chloride are combined with stirring. The temperature of the mixture soon rises; they cannot be allowed to rise above 90 C by suitable cooling. When self-heating no longer occurs, between 85 and 90 parts by weight slowly become 140 parts by weight powdered. dry potassium carbonate entered; then the mixture is stirred for a further two hours at water bath temperature.
500 parts of water are then added to dissolve the salt, the mixture is allowed to cool, the oil is separated from the salt solution after dilution with about 200 parts of ether, dried over potassium carbonate and distilled. With 8 mm pressure by 203 or with 3 mm pressure by 175, the product boils over as a colorless oil, which solidifies completely on cooling. From the loot: 220 parts by weight of 1-dibenzylaminoethanol-2, large crystals with a temperature of 46 to 47 C, easily soluble in ether and benzene and almost insoluble in water, recrystallisable from dilute alcohol.
The hydrochloric acid 1-dibenzylaminoethyl chloride formed from 1-dibenzylaminoethanol-2 with thionyl chloride in smooth reaction crystallizes from alcohol in flakes of F. P. 192 C.
2. 122 parts by weight of ethanolamine and 253 parts by weight of benzyl chloride are reacted, and the mixture is reheated on the water bath for two hours. After cooling, concentrated potassium carbonate solution and ether are added.
After separation and drying, the ether solution is distilled in vacuo over potassium carbonate and, after a preliminary run of about 85 parts by weight of benzyl chloride, gives 161 parts by weight of 1-dibenzylamino-2-ethanol at 3 mm from 170 to 175 ° C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE154820X | 1930-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH154820A true CH154820A (en) | 1932-05-31 |
Family
ID=5676549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH154820D CH154820A (en) | 1930-06-10 | 1931-06-08 | Process for the preparation of 1-dibenzylamino-ethan-2-ol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH154820A (en) |
-
1931
- 1931-06-08 CH CH154820D patent/CH154820A/en unknown
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