DE1069635B - Process for the preparation of 3-imidazolines. - Google Patents

Process for the preparation of 3-imidazolines.

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Publication number
DE1069635B
DE1069635B DE1958V0014472 DEV0014472A DE1069635B DE 1069635 B DE1069635 B DE 1069635B DE 1958V0014472 DE1958V0014472 DE 1958V0014472 DE V0014472 A DEV0014472 A DE V0014472A DE 1069635 B DE1069635 B DE 1069635B
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Prior art keywords
ether
imidazoline
imidazolines
araliphatic
cycloaliphatic
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DE1958V0014472
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German (de)
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Schönebeck/Elbe und Dipl.-Chem. Dr. Hermann Pfanz Hannover-Kirchrode Dipl.-Chem. Dr. Gerhard Kirchner
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Fahlberg List Veb
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Priority to DE1958V0014472 priority Critical patent/DE1069635B/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Description

Verfahren zur Herstellung von 3-Imidazolinen Es sind in der Literatur in großer Anzahl 2-Imidazoline beschrieben und auch eine Reihe von 4-Imidazolinen bekanntgeworden. Technisch gangbare Wege zur Herstellung von 3-Imidazolinen sind bisher nicht beschrieben.Process for the preparation of 3-imidazolines There are in the literature described in large numbers 2-imidazolines and also a number of 4-imidazolines known. Technically viable routes for the production of 3-imidazolines are not yet described.

Es wurde nun gefunden, daß sich derartige Verbindungen überraschend leicht und in guten Ausbeuten herstellen lassen, wenn man a-Aminoketone der allgemeinen Formel worin R1 und R4 beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische oder aromatische Reste sind, R4 auch H sein kann, R2 und R3 Wasserstoff oder beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische, aromatische oder heterocyclische Reste sind, mit Carbonylverbindungen der allgemeinen Formel worin RS und/oder Re Wasserstoff oder beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische, aromatische oder heterocyclische Reste darstellen, wobei auch R5 und Rs über eine Alkylenkette zum Ring geschlossen sein können, und Ammoniak zur Umsetzung bringt.It has now been found that such compounds can be prepared surprisingly easily and in good yields if α-aminoketones of the general formula are used where R1 and R4 are any optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radicals, R4 can also be H, R2 and R3 are hydrogen or any optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, with carbonyl compounds of the general formula where RS and / or Re represent hydrogen or any optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, where R5 and Rs can also be closed via an alkylene chain to form the ring, and ammonia reacts.

Wegen der häufig vorhandenen Instabilität der a-Aminoketone ist es zweckmäßig, die oben beschriebenen a-Aminoketone in Form ihrer Salze zur Anwendung zu bringen.Because of the common instability of the α-amino ketones, it is expedient to use the above-described a-amino ketones in the form of their salts bring to.

Die in erfindungsgemäßer «'eise hergestellten 3-Imidazoline der allgemeinen Formel, worin R, bis R6 die oben geschilderte Bedeutung haben, stellen wertvolle organische Zwischenprodukte dar oder können als solche in der Technik vielfältige Anwendung finden.The 3-imidazolines prepared in accordance with the invention of the general Formula in which R 1 to R 6 are as defined above are valuable Organic intermediates are or can be diverse as such in technology Find application.

Beispiel 1 1, 5-Dimethyl-4-phenyl-imidazolin-4-3 20 g (1/1o Mol) a-Methylaminopropiophenon-hydrochlorid werden in wenig Wasser gelöst und mit 3 g (1,11o Mol) Paraformaldehyd versetzt. Unter Rühren und Kühlen mit Wasser werden etwa 20 bis 30 ccm konzentriertes Ammoniak tropfenweise hinzugefügt. Es wird 1 Stunde nachgerührt. Danach wird das Reaktionsprodukt mit Äther oder einem anderen geeigneten Lösungsmittel aus dem Reaktionsgemisch extrahiert. Die Ätherlösung wird mit Natriumsulfat getrocknet. Schließlich wird nach Abtrennung des Trockenmittels der Äther abdestilliert, wobei eine gelbliche kristalline Masse zurückbleibt, die nach Abdrücken auf einem Tonteiler und Trocknen im Exsikkator bei 54 bis 55° C schmilzt. Rohausbeute 13 g = 75 °/o. Aus Äther/Petroläther umkristallisiert: F. 57°C. Analyse für C11H"Nz: Berechnet ... C 75,840/0, H 8,100/0, N 16,08°/o; gefunden ... C 75,93 %, H 8,13 °/o, N 16,13 °/a. Beispiel 2 1, 5-Dimethyl-2-pentamethylen-4-phenyl-imidazolin-4 -3 20 ga-Methyiaminopropiophenon-hydrocbloridwerden, wie im Beispiel 1 beschrieben, mit 9,8 g Cyclohexanon und etwa 20 bis 30 ccm konzentriertem Ammoniak umgesetzt. Der Destillationsrückstand des Ätherextraktes wird nicht kristallin. Er ist ein gelbes Öl, das sich gut im Vakuum destillieren läßt. Ausbeute 19 g = 78,5 Kp."o = 142° C. Analyse für C"H"Nz: Berechnet ... C 79,29 °/o, H 9,15 °/o, N 11,56 °/a; gefunden ... C 79,46 l)/o, H 9,02 °%, N 11,30 0/a. Beispiel 3 1,5-Dimethyl-2,4-diphenyl-imidazolin-d-3 20 g a-Methylaminopropiophenon-hydrochlorid werden, wie im Beispiel 1 beschrieben, mit 10,6 g frisch destilliertem Benzaldehyd und etwa 20 bis 30 ccm konzentriertem Ammoniak umgesetzt. Der gelbe ölige Destillationsrückstand des Ätherextraktes wird im Vakuum destilliert. Ausbeute 20 g = 800J0; Kp.l.O = 166' C. Analyse für C1,H18N2: Berechnet ... C 81,560/0, H 7,130j" N 11,19%; gefunden ... C 81,46 0/0, H 7,16 0/" N 11,05 0/0. Beispiel 4 1,5-Dimethyl-4-phenyl-2-(a-pyridyl)-imidazolin-d-3 20 g a-Methylaminopropiophenon-hydrochloridwerden mit 10,7 g frisch destilliertem a-Pyridinaldehyd und 20 ccm konzentriertem Ammoniak, wie im Beispiel 1 beschrieben, umgesetzt. Die Umsetzung verläuft stark exotherm. Es muß mit Wasser gekühlt werden.Example 1 1,5-Dimethyl-4-phenyl-imidazoline-4-3 20 g (1/10 mol) of α-methylaminopropiophenone hydrochloride are dissolved in a little water and 3 g (1.11o mol) of paraformaldehyde are added. While stirring and cooling with water, about 20 to 30 cc of concentrated ammonia are added dropwise. It is stirred for 1 hour. The reaction product is then extracted from the reaction mixture with ether or another suitable solvent. The ether solution is dried with sodium sulfate. Finally, after the drying agent has been separated off, the ether is distilled off, leaving a yellowish crystalline mass which, after being pressed onto a clay divider and drying in a desiccator, melts at 54 to 55 ° C. Crude yield 13 g = 75%. Recrystallized from ether / petroleum ether: mp 57 ° C. Analysis for C11H "Nz: Calculated ... C 75.840 / 0, H 8.100 / 0, N 16.08 ° / o; Found ... C 75.93%, H 8.13 ° / o, N 16.13 ° / a. Example 2 1,5-Dimethyl-2-pentamethylene-4-phenyl-imidazoline-4 -3 20 ga-methyiaminopropiophenone hydrochloride are reacted as described in Example 1 with 9.8 g of cyclohexanone and about 20 to 30 cc of concentrated ammonia. The distillation residue of the ether extract does not become crystalline. It is a yellow oil that can be easily distilled in a vacuum. Yield 19 g = 78.5 bp "o = 142 ° C. Analysis for C "H" Nz: Calculated ... C 79.29 ° / o, H 9.15 ° / o, N 11.56 ° / a; Found ... C 79.46 l) / o, H 9.02%, N 11.30 0 / a. Example 3 1,5-Dimethyl-2,4-diphenyl-imidazoline-d-3 20 g of α-methylaminopropiophenone hydrochloride are, as described in Example 1, with 10.6 g of freshly distilled benzaldehyde and about 20 to 30 cc of concentrated ammonia implemented. The yellow oily distillation residue of the ether extract is distilled in vacuo. Yield 20 g = 800IO; Bp.10 = 166 ° C. Analysis for C1, H18N2: Calculated ... C 81.560 / 0, H 7.130j "N 11.19%; Found ... C 81.46 0/0, H 7.16 0 / "N 11.05 0/0. Example 4 1,5-Dimethyl-4-phenyl-2- (a-pyridyl) -imidazoline-d-3 20 g of a-methylaminopropiophenone hydrochloride are mixed with 10.7 g of freshly distilled a-pyridine aldehyde and 20 cc of concentrated ammonia, as in Example 1 described, implemented. The implementation is highly exothermic. It has to be cooled with water.

Neben einer kleinen Menge einer kristallinen Substanz, die in Wasser und Äther nicht löslich ist, entsteht in guter Ausbeute das entsprechende 3-Imidazolin, das mit Äther, Benzol oder anderen geeigneten Lösungsmitteln extrahiert werden kann. Es wird daraus durch Destillation im Vakuum rein erhalten. Ausbeute 21 g (84%). Kp.o,$ = 172° C. Beim Stehen über Nacht wird die Substanz kristallin. Analyse für C"H17N3: Berechnet ... C 76,45 0/" H 6,82 0/" N 16,72 0/0; gefunden ... C 76,88 0/0, H 6,910/0, N 16,50 0/0. Beispiel 5 1,5-Dimethyl-2-(n-heptyl)-4-phenyl-imidazolin-d-3 20 g a-Methylaminopropiophenon-hydrochlorid werden mit 12,8 g n-Octylaldehyd und 20 ccm konzentriertem Ammoniak, wie im Beispiel l beschrieben, umgesetzt. Das Reaktionsprodukt wird mit Äther, Benzol oder anderen geeigneten Lösungsmitteln extrahiert und durch Destillation abgetrennt. Ausbeute 22 g (810/0); Kp."s = 145° C. Analyse für C"H"N2: Berechnet ... C 79,330/0, H 10,360;'0, N 10,280/0; gefunden ... C 79,15 0(0, H 10,250/" N 10,220/0. Beispiel 6 2,2-Pentamethylen-4-phenyl-imidazolin-d-3 21,5g eines Gemisches von a Aminoacetophenonhydrochlorid bzw. -hydrobromid werden in wenig Wasser gelöst und in dieser Form unter kräftigem Rühren tropfenweise einem vorgelegten Gemisch, bestehend aus 9,8 g Cyclohexanon, 30 ccm konzentriertem Ammoniak und 40 ccm Wasser, hinzugefügt. Es wird noch etwas nachgerührt, danach wird das Imidazolin in Äther aufgenommen, die Ätherlösung mit Na2S04 getrocknet und der Äther abdestilliert. Es bleiben 15,8g eines festen Rückstandes zurück; F. = 64 bis 66° C. Analyse für C"H"N2: Berechnet ... C 78,46 0/0, H 8,47 0/" N 13,07 0/0; gefunden ... C 78,250/0, H 8,580/0, N 13,120/0. Beispiel 7 4-Methyl-2,2-pentamethylen-5-phenyl-imidazolin-d-3 18,5 g a-Amino-a-phenylaceton-hydrochlorid werden mit 9,8g Cyclohexanon und 30 ccm konzentriertem Ammoniak in wäßrigem Medium, wie im Beispie16 beschrieben, umgesetzt. Das Reaktionsgemisch wird ausgeäthert und die Ätherlösung nach dem Trocknen destilliert. Das Imidazolin destilliert im Vakuum von 0,7 mm bei 145 bis 146° C. Ausbeute 16 g @ 70 0/0. Analyse für C"H"N2: Berechnet ... C 78,910%, H 8,830/0, N 12,27oo; gefunden ... C 78,570/0, H 8,950/0, N 12,170%0. Beispiel 8 1, 5-Dimethyl-2-(a-furanyl)-4-phenyl-imidazolin-d-3 20 g a-Methylaminopropiophenon-hydrochlorid werden, wie im Beispiel 1 beschrieben, mit 9,6 g Furfurol und 30 ccm konzentriertem Ammoniak umgesetzt. Das Umsetzungsprodukt wird mit Äther extrahiert, die Ätherlösung mit Natriumsulfat getrocknet und destilliert. Ausbeute 16 g 680/0; Kp."s = 153 bis 155° C. Analyse für C15H1sONa: Berechnet ... C 74,96 0/" H 6,73 0/0, N 11,66 0/0; gefunden ... C 74,750/0, H 6,71010, N 11,700/0. Beispiel 9 1,4-Diphenyl-5-methyl-2,2-pentamethylen-imidazolin-d-3 11,12 g a-Phenylaminopropiophenon wurden mit 18,6 g Cyclohexanon und 60 ccm verflüssigtem Ammoniak 6 Stunden in einem geschlossenen Gefäß bei 95° C geschüttelt (27 bis 30 atü). Durch Vakuumdestillation wurde aus dem Reaktionsgemisch neben einem geringen Teil der Ausgangsprodukte ein Produkt isoliert, das keinen einheitlichen Siedepunkt besaß und Ammoniak abspaltete. Kp."4 163 bis 169° C, nö = 1,5515.In addition to a small amount of a crystalline substance that is not soluble in water and ether, the corresponding 3-imidazoline is produced in good yield, which can be extracted with ether, benzene or other suitable solvents. It is obtained pure therefrom by distillation in vacuo. Yield 21g (84%). Kp.o, $ = 172 ° C. When standing overnight, the substance becomes crystalline. Analysis for C "H1 7 N3: Calculated ... C 76.45% / "H 6.82% /" N 16.72%; Found ... C 76.88 0/0, H 6.910/0, N 16.50 0/0. Example 5 1,5-Dimethyl-2- (n-heptyl) -4-phenyl-imidazoline-d-3 20 g of a-methylaminopropiophenone hydrochloride are mixed with 12.8 g of n-octylaldehyde and 20 cc of concentrated ammonia, as in the example l described, implemented. The reaction product is extracted with ether, benzene or other suitable solvents and separated off by distillation. Yield 22 g (810/0); Bp "s = 145 ° C. Analysis for C "H" N2: Calculated ... C 79.330 / 0, H 10.360, '0, N 10.280 / 0; Found ... C 79.15 O (O, H 10.250 / "N 10.220 / O. Example 6 2,2-pentamethylene-4-phenyl-imidazoline-d-3 21.5 g of a mixture of a aminoacetophenone hydrochloride or hydrobromide are dissolved in a little water and in this form, with vigorous stirring, a mixture consisting of 9, 8 g of cyclohexanone, 30 cc of concentrated ammonia and 40 cc of water are added. The mixture is stirred a little, then the imidazoline is taken up in ether, the ether solution is dried with Na2SO4 and the ether is distilled off. 15.8 g of a solid residue remain; F. = 64 to 66 ° C. Analysis for C "H" N2: Calculated ... C 78.46 0/0, H 8.47 0/0; "N 13.07 0/0; Found ... C 78.250 / 0, H 8.580 / 0, N 13.120 / 0. Example 7 4-Methyl-2,2-pentamethylene-5-phenyl-imidazoline-d-3 18.5 g of a-amino-a-phenylacetone hydrochloride are mixed with 9.8 g of cyclohexanone and 30 cc of concentrated ammonia in an aqueous medium, such as described in Example16, implemented. The reaction mixture is extracted with ether and the ethereal solution is distilled after drying. The imidazoline distills in a vacuum of 0.7 mm at 145 to 146 ° C. Yield 16 g @ 70 0/0. Analysis for C "H" N2: Calculated ... C 78.910%, H 8.830 / 0, N 12.27oo; Found ... C 78.570 / 0, H 8.950 / 0, N 12.170% 0. Example 8 1,5-Dimethyl-2- (a-furanyl) -4-phenyl-imidazoline-d-3 20 g of a-methylaminopropiophenone hydrochloride are, as described in Example 1, with 9.6 g of furfural and 30 cc of concentrated Ammonia implemented. The reaction product is extracted with ether, the ether solution is dried with sodium sulfate and distilled. Yield 16 g 680/0; Bp "s = 153 to 155 ° C. Analysis for C15H1sONa: Calculated ... C 74.96% "H 6.73 0/0, N 11.66 0/0; Found ... C 74.750 / 0, H 6.71010, N 11.700 / 0. Example 9 1,4-Diphenyl-5-methyl-2,2-pentamethylene-imidazoline-d-3 11.12 g of a-phenylaminopropiophenone were mixed with 18.6 g of cyclohexanone and 60 cc of liquefied ammonia in a closed vessel at 95 for 6 hours ° C shaken (27 to 30 atü). In addition to a small portion of the starting materials, a product which did not have a uniform boiling point and which split off ammonia was isolated from the reaction mixture by vacuum distillation. Bp "4 163 to 169 ° C, nö = 1.5515.

Aus dem Verhalten bei Umsetzungen ist zu schließen, daß es sich um ein entsprechendes Imidazolin handelt, das noch 1 Mol Ammoniak gebunden enthält. Analyse für C21 H27 N,: Berechnet ... C 78,45 0/" H 8,47 0/" N 13,07 0/0; gefunden ... C 78,75 0/" H 9,0 0/" N 13,0 0/0. From the behavior in reactions it can be concluded that it is a corresponding imidazoline which still contains 1 mol of ammonia bound. Analysis for C21 H27 N,: Calculated ... C 78.45% / "H 8.47% /" N 13.07%; Found ... C 78.75 0 / "H 9.0 0 /" N 13.0 0/0.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 3-Imidazolinen der allgemeinen Formel worin R1 und R4 beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische oder aromatische Reste sind, R4 auch H sein kann, R2 und R3 Wasserstoff oder beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische, aromatische oder heterocyclische Reste sind und R5 und/oder R, Wasserstoff oder beliebige, gegebenenfalls substituierte aliphatische, cycloaliphatische, araliphatische, aromatische oder heterocyclische Reste darstellen, wobei auch RS und RB über eine Alkylenkette zum Ring geschlossen sein können, dadurch gekennzeichnet, daB a-Aminoketone der allgemeinen Formel oder deren Salze mit Carbonylverbindungen der allgemeinen Formel in denen R1 bis RB die obige Bedeutung haben, und Ammoniak zur Umsetzung gebracht werden.PATENT CLAIM: Process for the preparation of 3-imidazolines of the general formula where R1 and R4 are any optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radicals, R4 can also be H, R2 and R3 are hydrogen or any optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals and R5 and / or R , Represent hydrogen or any optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, where RS and RB can also be closed via an alkylene chain to form a ring, characterized in that α-aminoketones of the general formula or their salts with carbonyl compounds of the general formula in which R1 to RB have the above meaning, and ammonia are made to react.
DE1958V0014472 1958-05-29 1958-05-29 Process for the preparation of 3-imidazolines. Pending DE1069635B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5849929A (en) * 1997-09-26 1998-12-15 Uniroyal Chemical Company, Inc. Process for the preparation of imidazoline nitroxyl
EP3372587A1 (en) 2017-03-09 2018-09-12 Centre National de la Recherche Scientifique (CNRS) 3-imidazolines as carbapenemases inhibitors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5849929A (en) * 1997-09-26 1998-12-15 Uniroyal Chemical Company, Inc. Process for the preparation of imidazoline nitroxyl
EP3372587A1 (en) 2017-03-09 2018-09-12 Centre National de la Recherche Scientifique (CNRS) 3-imidazolines as carbapenemases inhibitors
WO2018162670A1 (en) 2017-03-09 2018-09-13 Centre National De La Recherche Scientifique (Cnrs) 2- or 3-imidazolines as carbapenemases inhibitors

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