CH234936A - Process for the preparation of an amino compound. - Google Patents
Process for the preparation of an amino compound.Info
- Publication number
- CH234936A CH234936A CH234936DA CH234936A CH 234936 A CH234936 A CH 234936A CH 234936D A CH234936D A CH 234936DA CH 234936 A CH234936 A CH 234936A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino compound
- compound
- dibutylamine
- production
- preparation
- Prior art date
Links
- -1 amino compound Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N N-butyl-butylamine Natural products CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Aminoverbindung. Gegenstand dieses Patentes bildet ein Verfahren zur Herstellung einer Aminover- bindung, welches dadurch gekennzeichnet ist, dass man 1-Halogen-propyl=(3)-dibutylamin mit einem Metall umsetzt und die erhaltene Organometa=llverbindunb auf Benzophenon einwirken lässt.
Das so gewonnene Diphenyl-3,-dibutyl- aminopropyl-earbinol 'ist ein O'1 und bildet ein Hydrochlorid vom Smp. 158-159 .
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischenpro dukt zur Herstellung therapeutisch verwend barer Stoffe dienen. <I>Beispiel:</I> Zu 3;9 g (0,16 Mol) Magnesium, das mit Jod und Äthylbromid angeätzt wurde, wer den 30,9 g (0,15 Mol) 1-Chlor-propyl-,(3,)- dibutylamin in ä0 cm' trockenem Äther unter leichtem Erwärmen zugegeben.
Nach < ,:nigen Minuten werden portionenweise 18 g (0,1 Mol) Benzophenon in ä0 cm' trockenem Äther einlaufen gelassen bei einer Tempera- tur von 45 . Nach weiterem Erwärmen wäh rend 3 Stunden bei dieser Temperatur ist das Magnesium verbraucht. Die Metallverbin dung wird mit Eis und Salzsäure zerstört und die Base mit verdünnter Salzsäure aus gezogen.
Aus der salzsauren Lösung scheidet sich alsbald das Hydrochlorid des Diphenyl- 3@-dibutylaminopTopyl-earbinols ab, das ge sammelt und aus Chlaroform-Essigester um kristallisiert wird. Smp. 158-159 .
Process for producing an amino compound. The subject of this patent is a process for the production of an amino compound, which is characterized in that 1-halopropyl = (3) -dibutylamine is reacted with a metal and the resulting organometallic compound is allowed to act on benzophenone.
The diphenyl-3, -dibutyl-aminopropyl-earbinol 'obtained in this way is an O'1 and forms a hydrochloride of melting point 158-159.
The new compound is intended to find therapeutic use or serve as an intermediate product for the production of therapeutically usable substances. <I> Example: </I> To 3; 9 g (0.16 mol) of magnesium, which has been etched with iodine and ethyl bromide, 30.9 g (0.15 mol) of 1-chloropropyl -, ( 3,) - dibutylamine was added in 00 cm 'dry ether with gentle heating.
After a few minutes, 18 g (0.1 mol) of benzophenone are allowed to run in in portions in --0 cm 'of dry ether at a temperature of 45. After further heating for 3 hours at this temperature, the magnesium is used up. The metal connection is destroyed with ice and hydrochloric acid and the base is drawn off with dilute hydrochloric acid.
The hydrochloride of diphenyl-3 @ -dibutylaminopTopyl-earbinol separates from the hydrochloric acid solution, which is collected and recrystallized from chloroform / ethyl acetate. 158-159.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234936T | 1941-07-25 | ||
| CH232887T | 1941-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH234936A true CH234936A (en) | 1944-10-31 |
Family
ID=25727769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH234936D CH234936A (en) | 1941-07-25 | 1941-07-25 | Process for the preparation of an amino compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH234936A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2879294A (en) * | 1956-01-25 | 1959-03-24 | Mead Johnson & Co | 1, 1-diaryl-2-aminoalkanols |
-
1941
- 1941-07-25 CH CH234936D patent/CH234936A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2879294A (en) * | 1956-01-25 | 1959-03-24 | Mead Johnson & Co | 1, 1-diaryl-2-aminoalkanols |
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