CH184533A - Process for the preparation of a cyclic amine. - Google Patents
Process for the preparation of a cyclic amine.Info
- Publication number
- CH184533A CH184533A CH184533DA CH184533A CH 184533 A CH184533 A CH 184533A CH 184533D A CH184533D A CH 184533DA CH 184533 A CH184533 A CH 184533A
- Authority
- CH
- Switzerland
- Prior art keywords
- solution
- prepare
- works
- alcohol
- cyclic amine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- -1 cyclic amine Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- 230000003165 hydrotropic effect Effects 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OKYRLKFOPJMWQN-UHFFFAOYSA-N 8-bromooctan-1-amine Chemical compound NCCCCCCCCBr OKYRLKFOPJMWQN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZHVULPDNOFUIML-UHFFFAOYSA-N octane;hydrochloride Chemical compound Cl.CCCCCCCC ZHVULPDNOFUIML-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate 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
- 150000003673 urethanes Chemical class 0.000 description 1
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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines cyclischen Amins. Gegenstand des vorliegenden Patentes bildet. ein Verfahren zur Herstellung eines cyclischen Amins, welches dadurch gekenn zeichnet ist, dass man einen reaktionsfähigen Ester des Aminoalkohols der Formel HO- (CHz)s-NHa in verdünnter Lösung erwärmt. Das gebildete Cyclo-octamethylenimin ist identisch mit der nach dem Patent Nr.176831 erhaltenen Base.
Zweckmässig wird in Gegenwart von säurebindenden Mitteln gearbeitet; wobei vorhandene Salze des veresterten Amino- alkohols vorerst in die freie Ausgangsbase übergehen. Geeignete säurebindende Mittel sind z. B. die Hydroxyde oder Carbonate von Alkalien oder Erdalkalien, Magnesiumoxyd oder dergleichen.
Als reaktionsfähige Ester kommen die jenigen der Halogenwasserstoffsäuren; der Arylsulfonsäure usw. in Betracht.
Es ist für den Erfolg des Verfahrens wesentlich, dass die Lösung der Base genü- gend verdünnt und die Base vollkommen gelöst ist.
Für das Verfahren geeignete Lösungs mittel sind z. B. Äther, Benzol, Petroläther, Butyläther, wässerige Alkohole, wässerige Lösungen hydrotroper organischer Verbin dungen, wie Natriumbenzoat, Urethane, Al- kylbarnstoffe, aliphatische Fettsäureamide und dergleichen.
<I>Beispiel</I> Das Hydrochlorid des 1-Brom-8-amino- octans wird unter Kühlung und Rühren in benzolischer Suspension mit 1 Mol verdünnter wässeriger Natronlauge umgesetzt. Die so erhaltene benzolische Lösung des freien Amins wird getrocknet und mit reichlich Benzol verdünnt. Dann wird so lange auf 40-500 erwärmt, bis die Umwandlung in das Hydrobromid des Pentadecamethylenimins vollständig ist.
Es ist dies daran zu erken nen, dass eine weitere Vermehrung des ent standenen Niederschlages nicht mehr eintritt Das aus dem ausgefallenen Salz durch Zu satz überschüssiger wässeriger Lauge in Freiheit gesetzte Cyclo-octamethylenimin sie det bei 70 (20 mm) und liefert ein bei 148-149 schmelzendes Pikrat.
<I>Beispiel 2:</I> 10 g l#ydruchlorid des 1-Brom-8-amino- octans werden in etwa 3 Liter Butylalkohol mit 50 cm' normaler Natronlauge (2 Mol) mehrere Stunden gekocht. Zur Aufarbeitung kann man mit Salzsäure ansäuern und die Lösung des Hydrochlorids eindampfen. Die Isolierung des reinen Amins geschieht nach den Angaben von Beispiel 1. Beispiel <I>3</I> 10 g Hydrochlorid des 1-Brom-8-aminö octans werden in etwa 3 Liter Methylalko hol oder Äthylalkohol mit 50 cm3 normaler Natronlauge versetzt.
Die Reaktionslösung wird einige Tage bei etwa 501 , gehalten Hierauf wird mit Salzsäure angesäuert und die Lösung des Hydrochlorids eingedampft. Die Isolierung des cyclischen Amins geschieht nach den Angaben des Beispiels 1.
Process for the preparation of a cyclic amine. Subject of the present patent forms. a process for the preparation of a cyclic amine, which is characterized in that a reactive ester of the amino alcohol of the formula HO- (CHz) s-NHa is heated in dilute solution. The cyclo-octamethyleneimine formed is identical to the base obtained according to Patent No. 176831.
It is expedient to work in the presence of acid-binding agents; existing salts of the esterified amino alcohol initially being transferred to the free starting base. Suitable acid-binding agents are, for. B. the hydroxides or carbonates of alkalis or alkaline earths, magnesium oxide or the like.
The reactive esters are those of the hydrohalic acids; the aryl sulfonic acid, etc. into consideration.
It is essential for the success of the process that the solution of the base is sufficiently diluted and the base is completely dissolved.
Suitable solvents for the process are, for. B. ether, benzene, petroleum ether, butyl ether, aqueous alcohols, aqueous solutions of hydrotropic organic compounds, such as sodium benzoate, urethanes, alkyl barn materials, aliphatic fatty acid amides and the like.
<I> Example </I> The hydrochloride of 1-bromo-8-amino-octane is reacted with 1 mol of dilute aqueous sodium hydroxide solution in a benzene suspension while cooling and stirring. The benzene solution of the free amine thus obtained is dried and diluted with plenty of benzene. The mixture is then heated to 40-500 until the conversion into the hydrobromide of pentadecamethyleneimine is complete.
This can be seen from the fact that the precipitate that has formed no longer increases. The cyclo-octamethyleneimine released from the precipitated salt by the addition of excess aqueous alkali melts at 70 (20 mm) and provides a 148- 149 melting picrate.
Example 2: 10 g of 1-bromo-8-amino-octane chloride are boiled in about 3 liters of butyl alcohol with 50 cm of normal sodium hydroxide solution (2 mol) for several hours. For working up, you can acidify with hydrochloric acid and evaporate the solution of the hydrochloride. The pure amine is isolated as described in Example 1. Example <I> 3 </I> 10 g of 1-bromo-8-aminö octane hydrochloride are mixed with 50 cm3 of normal sodium hydroxide solution in about 3 liters of methyl alcohol or ethyl alcohol.
The reaction solution is kept for a few days at about 50 l. It is then acidified with hydrochloric acid and the solution of the hydrochloride is evaporated. The cyclic amine is isolated as described in Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH184533T | 1933-11-25 | ||
| CH178897T | 1933-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184533A true CH184533A (en) | 1936-05-31 |
Family
ID=25720221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184533D CH184533A (en) | 1933-11-25 | 1933-11-25 | Process for the preparation of a cyclic amine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH184533A (en) |
-
1933
- 1933-11-25 CH CH184533D patent/CH184533A/en unknown
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