CH307854A - 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
CH307854A
CH307854A CH307854DA CH307854A CH 307854 A CH307854 A CH 307854A CH 307854D A CH307854D A CH 307854DA CH 307854 A CH307854 A CH 307854A
Authority
CH
Switzerland
Prior art keywords
cyano
cyclohexyl
alkylamine
preparation
chloro
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 CH307854A publication Critical patent/CH307854A/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- (l-Cyan-cyclohexyl)-alkylamins.   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines Naeylierten N-   (1-Cyan-eyelohexyl)-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 Reaktion abspaltende Reste bedeuten.



   Man kann beispielsweise   N-(l-Cyan-eyclo-       hexyl)-methylamin (X = H) mit p-Chlor-phe-      nylessigsaure (Y = OH)    in Gegenwart eines   wasserabspaltenden Mittels umsetzen    oder das erwähnte Amin mit einem reaktiven funktionellen Derivat der p-Chlor-phenylessigsäure, z. B. einem Halogenid, einem Ester, einem   Anhpdrid,    einem Amid usf., zur Reaktion bringen.



   Es ist weiterhin auch möglich, ein   N- (1-    Cyan-eyelohexyl)-N-methyl-carbaminsäurehalogenid (X = COHal) mit p-Chlor-phenylessigsäure oder einem p-chlor-phenylessigsaurem Salz zur Umsetzung zu bringen, wobei unter Abspaltung von Kohlendioxyd das ge  wünschte    Endprodukt in guter Ausbeute gebildet wird.



   Das so erhaltene N-p-Chlor-phenacetyl-N    (1-cyan-eyclohexyl)-methylamin    bildet farblose Kristalle, die, aus   verdünntemÄthanol    umkristallisiert, bei 143-144  schmelzen. Es soll als Insektenvergrämungsmittel Verwendungfinden.



   Beispiel 1 :
Eine Lösung von 2 Mol N-   (1-Cyan-cyclo-    hexyl)-methylamin in der doppelten Menge Benzol wird unter Kühlung tropfenweise mit einer   Losung    von 1 Mol p-Chlor-phenylessigsäurechlorid in Benzol versetzt. Das Hydrochlorid des im Überschuss 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-p-Chlor-phenacetyl-N- (1-      cyan-cyelohexyl)-methylamin    in farblosen, bei 143-144  schmelzenden Kristallen.



   Beispiel 2 :
Das N-p-Chlor-phenacetyl-N- (1-cyan-cyclo  hexyl)-methylamin    gewinnt man auch durch mehrstündiges Erhitzen von   N- (1-Cyan-cyclo-    hexyl)-N-methyl-carbaminsäurechlorid mit seharf getrocknetem   p-chlor-phenylessigsaurem    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-cyclohexyl) -alkylamine.



   The present patent relates to a process for the preparation of a Naeylated N- (1-cyano-eyelohexyl) -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- (l-cyano-eyclohexyl) -methylamine (X = H) can be reacted with p-chloro-phenylacetic acid (Y = OH) in the presence of a dehydrating agent or the amine mentioned with a reactive functional derivative of p-chloro-phenylacetic acid, e.g. B. a halide, an ester, an anhpdride, an amide, etc., to react.



   It is also possible to react an N- (1-cyano-eyelohexyl) -N-methyl-carbamic acid halide (X = COHal) with p-chloro-phenylacetic acid or a p-chloro-phenylacetic acid salt, with elimination of Carbon dioxide the desired end product is formed in good yield.



   The N-p-chloro-phenacetyl-N (1-cyano-cyclohexyl) -methylamine thus obtained forms colorless crystals which, when recrystallized from dilute ethanol, melt at 143-144. 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 treated dropwise with a solution of 1 mole of p-chloro-phenylacetic acid 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. A colorless oil remains as a residue, which slowly solidifies. The solidified mass is recrystallized from dilute ethanol.



  The N-p-chloro-phenacetyl-N- (1-cyano-cyelohexyl) -methylamine is thus obtained in colorless crystals melting at 143-144.



   Example 2:
The Np-chloro-phenacetyl-N- (1-cyano-cyclohexyl) -methylamine is also obtained by heating N- (1-cyano-cyclohexyl) -N-methyl-carbamic acid chloride for several hours with carefully dried p-chloro Sodium phenylacetic acid 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-acy- lierten N- (1-Cyan-cyelohexyl)-alkylamins, dadurch gekennzeichnet, dass man eine Verbin dung 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 N- (1-cyano-cyelohexyl) -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-p-Chlor-phenaeetyl-N (1-cyan-cyelohexyl)-methylamin bildet farblose Kristalle, die, aus verdünntem Athanol umkristallisiert, bei 143-144 schmelzen. Es soll als Insektenvergrämungsmittel Verwen- dung finden. The N-p-chloro-phenaeetyl-N (1-cyano-cyelohexyl) -methylamine thus obtained forms colorless crystals which, recrystallized from dilute ethanol, melt at 143-144. It is said to be used as an insect repellent.
CH307854D 1952-01-11 1952-01-11 Process for the preparation of an N-acylated N- (1-cyano-cyclohexyl) -alkylamine. CH307854A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH303183T 1952-01-11
CH307854T 1952-01-11

Publications (1)

Publication Number Publication Date
CH307854A true CH307854A (en) 1955-06-15

Family

ID=25734586

Family Applications (1)

Application Number Title Priority Date Filing Date
CH307854D CH307854A (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) CH307854A (en)

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