DE1024977B - Process for the production of tertiary diamines - Google Patents

Process for the production of tertiary diamines

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Publication number
DE1024977B
DE1024977B DEN7445A DEN0007445A DE1024977B DE 1024977 B DE1024977 B DE 1024977B DE N7445 A DEN7445 A DE N7445A DE N0007445 A DEN0007445 A DE N0007445A DE 1024977 B DE1024977 B DE 1024977B
Authority
DE
Germany
Prior art keywords
methyl
ergw
vol
acids
octadecyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEN7445A
Other languages
German (de)
Inventor
Godfrey Fred Grail
Floyd Edmond Anderson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nepera Chemical Co Inc
Original Assignee
Nepera Chemical Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nepera Chemical Co Inc filed Critical Nepera Chemical Co Inc
Publication of DE1024977B publication Critical patent/DE1024977B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/132—Amines having two or more amino groups, e.g. spermidine, putrescine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

DEUTSCHESGERMAN

Die Erfindung betrifft ein Verfahren zur Herstellung von Verbindungen der FormelThe invention relates to a process for the preparation of compounds of the formula

18 H37 R18 H 3 7 R

)n —CH2-CH2-N;
CH,' R) n -CH 2 -CH 2 -N;
CH, 'R

Verfahren zur Herstellung
von tertiären DiaminenMethod of manufacture
of tertiary diamines

worin R eine Methyl- oder Äthylgruppe bedeutet, und insbesondere des N-Octadecyl-N-methyl-N'jN'dimetlryläthylendiamins. Diese Verbindungen zeichnen sich in vivo durch sehr gute antivirale Eigenschaften aus. Diese antivirale Aktivität kommt insbesondere gegenüber dem Virus der Newcastle-Krankheit bei Geflügel, gegenüber dem Mumpsvirus und gegenüber dem Virus der Mäusepneumonitis zum Ausdruck.wherein R is a methyl or ethyl group, and in particular N-octadecyl-N-methyl-N'jN'dimetlryläthylendiamins. These compounds are distinguished in vivo by very good antiviral properties. These antiviral activity is particularly opposed to the Newcastle disease virus in poultry the mumps virus and the mouse pneumonitis virus.

Da das N-Octadecyl-N-methyl-N'.N'-dimethyl-äthylendiamin sowohl mit organischen als auch mit anorganischen Säuren Salze bildet, die nur einen geringen Geschmack odei Geruch aufweisen, kann diese Verbindung dem Hühnerfutter zugemengt oder in Form des wasserlöslichen Salzes dem für das Geflügel bestimmten Wasser zugesetzt werden, um die Wirkungen dieser Krankheiten zu unterdrücken oder zu lindern.Since the N-octadecyl-N-methyl-N'.N'-dimethyl-ethylenediamine Forms salts with both organic and inorganic acids, which only have a poor taste odei have a smell, this compound can be added to the chicken feed or in the form of the water-soluble Salt can be added to the water intended for poultry to reduce the effects of these diseases suppress or alleviate.

Diese Verbindung kann auch in Form von Pillen, Tabletten und Kapseln, gegebenenfalls in Verbindung mit anderen therapeutisch wirksamen Verbindungen, unter Verwendung der üblichen festen therapeutischen Trägermaterialien, wie Talk, Lactose, Dextrose, Magnesiumstearat u. dgl., angewendet werden.This compound can also be in the form of pills, tablets and capsules, optionally in conjunction with other therapeutically active compounds, using the usual solid therapeutic carrier materials, such as talc, lactose, dextrose, magnesium stearate and the like can be used.

Die Verbindungen können durch Umsetzung eines /J-Dimethylaminoäthylhalogem'ds, wie des Chlorids oder Bromids, mit Octadecyl-methyl-amin bei einer Temperatur zwischen 140 und 180° erhalten werden. Die Reaktion kann in einem inerten Lösungsmittel wie Xylol und einem Autoklav unter Druck durchgeführt werden. Sie dauert etwa 8 bis 40 oder sogar 60 Stunden.The compounds can by reacting a / I-Dimethylaminoäthylhalogem'ds, such as the chloride or Bromide, with octadecyl-methyl-amine at one temperature between 140 and 180 ° can be obtained. The reaction can be carried out in an inert solvent such as xylene and a Autoclave can be carried out under pressure. It takes about 8 to 40 or even 60 hours.

Zur Isolierung des Reaktionsproduktes wird die abgekühlte Reaktionsmischung vorzugsweise durch Zugabe von Natronlauge alkalisch gemacht, die wäßrige Mischung von der Xylolschicht abgetrennt und ausgeäthert. Der Ätherextrakt wird mit der Xylolschicht vereinigt, der Äther und das Xylol sowie das nicht umgesetzte Octadecyl-methyl-amin bei gewöhnlichem und das N-Octadecyl-N-methyl-N',N'-dimethyl-äthylendiamin bei vermindertem Druck abdestilliert.To isolate the reaction product, the cooled reaction mixture is preferably added by adding made alkaline by sodium hydroxide solution, the aqueous mixture separated from the xylene layer and extracted with ether. Of the The ether extract is combined with the xylene layer, the ether and the xylene as well as the unreacted octadecyl-methyl-amine with ordinary and the N-octadecyl-N-methyl-N ', N'-dimethyl-ethylenediamine distilled off at reduced pressure.

Zur Bildung von Salzen mit verstärkter Wasserlöslichkeit können als anorganische Säuren Schwefel- und Salzsäure ebenso wie Jodwasserstoff-, Phosphor- oder Bromwasserstoffsäure und als organische Säuren Wein-, Malein-, Milch-, Essig-, Propion-, Butter-, Bernstein-, IJndecylen- und Zitronensäure Verwendung finden.For the formation of salts with increased solubility in water, sulfuric and hydrochloric acids can be used as inorganic acids as well as hydriodic, phosphoric or hydrobromic acid and, as organic acids, tartaric, Maleic, lactic, vinegar, propionic, butyric, succinic, indecylenic and citric acids are used.

Anmelder:Applicant:

Nepera Chemical Co., Inc.,
Yonkers, N. Y. (V. St. A.)Nepera Chemical Co., Inc.,
Yonkers, NY (V. St. A.)

Vertreter:Representative:

Dr. G. W. Lotterhos und Dr.-Ing. H. W. Lotterhos,
Patentanwälte, Frankfurt/M., Lichtensteinstr. 3Dr. GW Lotterhos and Dr.-Ing. HW Lotterhos,
Patent attorneys, Frankfurt / M., Lichtensteinstr. 3

Beanspruchte Priorität:
V. St. v. Amerika vom 25. Februar 1953Claimed priority:
V. St. v. America February 25, 1953

Godfrey Fred Grail, New York, N. Y.,Godfrey Fred Grail, New York, N.Y.,

und Floyd Edmond Anderson, Yonkers, N. Y. (V. St. A.), sind als Erfinder genannt wordenand Floyd Edmond Anderson, Yonkers, N.Y. (V. St. A.), are named inventors

22

Das Verfahren der Erfindung soll an nachfolgendem Beispiel erläutert werden.The method of the invention will be explained using the following example.

Beispielexample

237 Gewichtsteile Octadecyl-methyl-amin werden in etwa 120 Gewichtsteile Xylol suspendiert, dann 45 Gewichtsteile /3-Dimethylaminoäthylchlorid zugefügt, die dabei erhaltene Mischung gründlich gemischt und in einem Autoklav 24 Stunden auf 150 bis 160° erhitzt. Nach Abkühlung der Reaktionsmischung stellt man das pH durch Zugabe von wäßriger 40%iger Natronlauge auf 11,0 ein, extrahiert die alkalische Mischung dreimal mit Äther und trocknet die vereinigten Ätherextrakte über Kaliumhydroxyd. Man trennt die flüssige Phase von dem festen Kaliumhydroxyd ab, destilliert zunächst den Äther und anschließend das Xylol ab. Der Rückstand wird einer Vakuumdestillation unterworfen, wobei das N-Octadecyl-N-methyl-N'.N'-dimethyl-äthylen-diamin bei einem Druck von 0,6 mm Hg bei 177 bis 178° übergeht. Das Reaktionsprodukt ist eine klare Flüssigkeit, die sich in Äther, Alkohol, Benzol sowie anderen üblichen organischen Lösungsmitteln löst, jedoch in Wasser unlöslich ist. Die sauren Salze dieses Diamins sind dagegen wasserlöslich.237 parts by weight of octadecyl-methyl-amine are suspended in about 120 parts by weight of xylene, then 45 parts by weight of 3-dimethylaminoethyl chloride are added, the resulting mixture is mixed thoroughly and heated in an autoclave to 150 to 160 ° for 24 hours. After cooling the reaction mixture to provide the p H by addition of aqueous 40% sodium hydroxide solution to 11.0 A, the alkaline mixture extracted three times with ether and the combined ether extracts over potassium hydroxide. The liquid phase is separated from the solid potassium hydroxide, first the ether and then the xylene are distilled off. The residue is subjected to vacuum distillation, the N-octadecyl-N-methyl-N'.N'-dimethyl-ethylene-diamine passing over at a pressure of 0.6 mm Hg at 177 to 178 °. The reaction product is a clear liquid that dissolves in ether, alcohol, benzene and other common organic solvents, but is insoluble in water. The acid salts of this diamine, on the other hand, are water-soluble.

Claims (4)

PATENTANSPRÜCHE:PATENT CLAIMS: 1. Verfahren zur Herstellung von tertiären Diaminen, dadurch gekennzeichnet, daß man Octadecyl-1. Process for the preparation of tertiary diamines, characterized in that octadecyl 709 907/+27709 907 / + 27 methyl-amin vorzugsweise unter erhöhtem Druck mit einem Dialkylaminoäthylhalogenid zu Verbindungen der Formelmethyl-amine, preferably under increased pressure, with a dialkylaminoethyl halide to form compounds the formula L18 H3 L 18 H 3 CH,CH, N-CH9-CH9-N;N-CH 9 -CH 9 -N; worin R eine Methyl- oder Äthylgruppe bedeutet, umsetzt und das erhaltene Reaktionsprodukt in bekannter Weise in seine wasserlöslichen Salze überführt. wherein R is a methyl or ethyl group, and the reaction product obtained in known Way converted into its water-soluble salts. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Reaktion in Gegenwart eines inerten organischen Lösungsmittels, vorzugsweise Xylol, durchführt.2. The method according to claim 1, characterized in that that the reaction in the presence of an inert organic solvent, preferably Xylene. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man zur Salzbildung an 01 ganische Säuren, wie Schwefel-, Salz-, Jodwasserstoff-, Phosphor- oder Bromwasserstoffsäure, oder organische Säuren, wie Wein-, Malein-, Milch-, Essig-, Propion-, Butter-, Bernstein-, Undecylen-, Zitronen-, Benzoe-, Gentisin-, Salicyl-, Resorcyl-, Phenylessig-, Mandel-, Zimt-, Hydrozimt-, Isocinchomeron- oder Chinolinsäure, verwendet.3. The method according to claim 1 or 2, characterized in that for salt formation to 01 ganische Acids such as sulfuric, hydrochloric, hydroiodic, phosphoric or hydrobromic acid, or organic Acids such as wine, maleic, milk, vinegar, propionic, butter, amber, undecylene, lemon, benzoin, Gentisic, salicylic, resorcylic, phenylacetic, almond, cinnamon, hydrocinnamic, isocinchomeronic or quinolinic acid, used. In Betracht gezogene Druckschriften:Considered publications: Deutsche Patentschrift Nr. 547 987;German Patent No. 547,987; Beilstein, Handbuch der organischen Chemie, 4.Auflage, Ergw. I, Bd. 4, S. 416; Ergw. II, Bd. Beilstein, Handbook of Organic Chemistry, 4th edition, Ergw. I, Vol. 4, p. 416; Ergw. II, vol. 4, S. 691;4, p. 691; Journ. Pharmacol. Experiment. Therap., 103 (1951), S. 288 bis 292.Journ. Pharmacol. Experiment. Therap., 103 (1951), pp. 288-292.
DEN7445A 1953-02-25 1953-07-10 Process for the production of tertiary diamines Pending DE1024977B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US1024977XA 1953-02-25 1953-02-25

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DE1024977B true DE1024977B (en) 1958-02-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025426A1 (en) * 1993-04-28 1994-11-10 Alcon Laboratories, Inc. Diamines as antimicrobial agents and use thereof in ophthalmic composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE547987C (en) * 1930-05-07 1932-04-01 I G Farbenindustrie Akt Ges Process for the preparation of derivatives of high molecular weight aliphatic amines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE547987C (en) * 1930-05-07 1932-04-01 I G Farbenindustrie Akt Ges Process for the preparation of derivatives of high molecular weight aliphatic amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994025426A1 (en) * 1993-04-28 1994-11-10 Alcon Laboratories, Inc. Diamines as antimicrobial agents and use thereof in ophthalmic composition
US5900213A (en) * 1993-04-28 1999-05-04 Alcon Laboratories, Inc. Use of diamines to disinfect and clean contact lenses and preserve ophthalmic compositions

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