CH307853A - Process for the preparation of an N-acylated N- (1-cyano-cyclohexyl) -alkylamine. - Google Patents

Process for the preparation of an N-acylated N- (1-cyano-cyclohexyl) -alkylamine.

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Publication number
CH307853A
CH307853A CH307853DA CH307853A CH 307853 A CH307853 A CH 307853A CH 307853D A CH307853D A CH 307853DA CH 307853 A CH307853 A CH 307853A
Authority
CH
Switzerland
Prior art keywords
cyclohexyl
cyano
alkylamine
preparation
acylated
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
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 Cilag Ag filed Critical Cilag Ag
Publication of CH307853A publication Critical patent/CH307853A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  



  Verfahren zur Herstellung eines   N-acylierten      N-      (1-Cyan-cyelohexyl)-alkylamins.   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines Naeylierten N- (1-Cyan-cyclohexyl)-alkylamins, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 mit einer Verbindung der Formel
EMI1.2     
 umsetzt, wobei X und Y sich bei der   Reak-    tion abspaltende Reste bedeuten.



   Man kann beispielsweise N-(1-Cyan-cyclo  hexyl)-methylamin (X=H)    mit o-Chlor-benzoesäure   (Y= OH)    in Gegenwart eines wasserabspaltenden Mittels umsetzen oder das erwähnte Amin mit einem reaktiven funktionellen Derivat der   o-Chlor-benzoesäure,    z.   B.    einem Halogenid, einem Ester, einem Anhydrid, einem Amid usf., zur Reaktion bringen.



   Es ist weiterhin auch   moglich,    ein   N- (1-       Cyan-eyelohexyl)-N-methyl-earbaminsäure-    halogenid   (X    = COHal) mit o-Chlor-benzoesäure oder einem o-chlor-benzoesauren Salz zur Umsetzung zu bringen, wobei unter Abspaltung von Kohlendioxyd das gewünschte Endprodukt in guter Ausbeute gebildet wird.



   Das so erhaltene N-o-Chlor-benzoyl-N-   (1-      cyan-cyclohexyl)-methylamin    bildet farblose Kristalle, die, aus verdünntem Äthanol umkristallisiert, bei 99, 5-101,   5     schmelzen. Es soll als Insektenvergrämungsmittel Verwendung    finden.



  Beispiel 1:   
Eine   Losung    von 2 Mol N- (1-Cyan  cyclohexyl)-methylamin    in der doppelten Menge Benzol wird unter Kiihlung   tropfen-    weise mit einer Lösung von   1    Mol o-Chlorbenzoylchlorid in Benzol versetzt. Das Hydrochlorid des im   Übersehuss    angewandten Amins fällt aus und wird nach Beendigung der Reaktion abgesaugt. Das Benzolfiltrat wird nach dem Waschen mit verdünnter Natronlauge und Wasser getrocknet und dann eingedampft. Als Rückstand bleibt ein farbloses   Öl,    das langsam erstarrt. Die verfestigte Masse wird aus verdünntem Äthanol umkristallisiert.

   Man erhält so das   N-o-Chlor-benzoyl-N- (1-cyan-cyclo-      hexyl)-methylamin    in farblosen, bei 99, 5 bis 101,   5     schmelzenden Kristallen.



   Beispiel 2 :
Das N-o-Chlor-benzoyl-N-   (1-cyan-cyclo-    hexyl)-methylamin gewinnt man auch durch mehrstündiges Erhitzen von N- (1-Cyan-cyclo  hexyl)-N-methyl-carbaminsäureehlorid    mit scharf getrocknetem o-chlorbenzoesaurem Natrium in Xylol. Die Aufarbeitung kann, nach Entfernen des gebildeten   Kochsalzes,    wie in Beispiel   1    angegeben erfolgen.



  



  Process for the preparation of an N-acylated N- (1-cyano-cyelohexyl) -alkylamine.



   The subject of the present patent is a process for the preparation of a Naeylated N- (1-cyano-cyclohexyl) -alkylamine, which is characterized in that a compound of the formula
EMI1.1
 with a compound of the formula
EMI1.2
 converts, where X and Y are radicals which are split off in the reaction.



   For example, N- (1-cyano-cyclohexyl) -methylamine (X = H) can be reacted with o-chloro-benzoic acid (Y = OH) in the presence of a dehydrating agent or the amine mentioned with a reactive functional derivative of o-chlorine benzoic acid, e.g. B. a halide, an ester, an anhydride, an amide, etc., to react.



   It is also possible to react an N- (1-cyano-eyelohexyl) -N-methyl-earbamic acid halide (X = COHal) with o-chloro-benzoic acid or an o-chloro-benzoic acid salt, with Elimination of carbon dioxide the desired end product is formed in good yield.



   The N-o-chloro-benzoyl-N- (1-cyano-cyclohexyl) -methylamine obtained in this way forms colorless crystals which, when recrystallized from dilute ethanol, melt at 99.55-101.5. It is said to be used as an insect repellent.



  Example 1:
A solution of 2 moles of N- (1-cyano-cyclohexyl) -methylamine in twice the amount of benzene is admixed dropwise with a solution of 1 mole of o-chlorobenzoyl chloride in benzene while cooling. The hydrochloride of the amine used in excess precipitates and is filtered off with suction after the reaction has ended. The benzene filtrate is washed with dilute sodium hydroxide solution and water, dried and then evaporated. The residue is a colorless oil that slowly solidifies. The solidified mass is recrystallized from dilute ethanol.

   The N-o-chloro-benzoyl-N- (1-cyano-cyclohexyl) -methylamine is obtained in this way in colorless crystals which melt at 99.5 to 101.5.



   Example 2:
The no-chloro-benzoyl-N- (1-cyano-cyclohexyl) -methylamine is also obtained by heating N- (1-cyano-cyclohexyl) -N-methyl-carbamic acid chloride with sharply dried sodium o-chlorobenzoate for several hours in xylene. The work-up can be carried out as indicated in Example 1 after the sodium chloride formed has been removed.

Claims (1)

PATENTANSPRUCH : Verfahren zur Herstellung eines N-acylier- t-en N- (1-Cyan-cyclohexyl)-alkylamins, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.1 mit einer Verbindung der Formel EMI2.2 umsetzt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. PATENT CLAIM: Process for the preparation of an N-acylated t-en N- (1-cyano-cyclohexyl) -alkylamine, characterized in that a compound of the formula EMI2.1 with a compound of the formula EMI2.2 converts, where X and Y are radicals which are split off in the reaction. Das so erhaltene N-o-Chlor-benzoyl-N- (l- eyan-cyclohexyl)-methylamin bildet farblose Kristalle, die aus verdünntem Äthanol umkri stallisiert bei 99, 5-101, 5 schmelzen. Es soll als Insektenvergrämungsmittel Verwendung finden. The N-o-chloro-benzoyl-N- (l-eyan-cyclohexyl) -methylamine thus obtained forms colorless Crystals that umkri crystallized from dilute ethanol at 99, 5-101, 5 melt. It is said to be used as an insect repellent.
CH307853D 1952-01-11 1952-01-11 Process for the preparation of an N-acylated N- (1-cyano-cyclohexyl) -alkylamine. CH307853A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH307853T 1952-01-11
CH303183T 1952-01-11

Publications (1)

Publication Number Publication Date
CH307853A true CH307853A (en) 1955-06-15

Family

ID=25734585

Family Applications (1)

Application Number Title Priority Date Filing Date
CH307853D CH307853A (en) 1952-01-11 1952-01-11 Process for the preparation of an N-acylated N- (1-cyano-cyclohexyl) -alkylamine.

Country Status (1)

Country Link
CH (1) CH307853A (en)

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