DE881041C - Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes - Google Patents

Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes

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Publication number
DE881041C
DE881041C DESCH105A DESC000105A DE881041C DE 881041 C DE881041 C DE 881041C DE SCH105 A DESCH105 A DE SCH105A DE SC000105 A DESC000105 A DE SC000105A DE 881041 C DE881041 C DE 881041C
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DE
Germany
Prior art keywords
phenyl
cyclohexylamine
cyclohexylaminopropanes
substituted
preparation
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.)
Expired
Application number
DESCH105A
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German (de)
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DE1606144U (en
Inventor
Aladar Dr Skita
Werner Dr Stuehmer
Wilhelm Dr Kaupmann
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Individual
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Individual
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Priority to DESCH105A priority Critical patent/DE881041C/en
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Publication of DE881041C publication Critical patent/DE881041C/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von C3-substituierten 1-Phenyl-3-N-cyclohexylaminopropanen Es ist bekannt, daß a, ß-ungesättigte Ketone leicht Amine an die Doppelbindung anzulagern vermögen. So liefert z. B. Benzalacetophenon mit Cyclohexylamin i, 3-Diphenyl-3-cyclohexylaminopropanon-(i).Process for the preparation of C3-substituted 1-phenyl-3-N-cyclohexylaminopropanes It is known that α, ß-unsaturated ketones easily add amines to the double bond capital. For example, B. Benzalacetophenone with cyclohexylamine i, 3-diphenyl-3-cyclohexylaminopropanone- (i).

Nicht bekannt und auch nicht zu erwarten war daher die Feststellung, daß bei a, ß-ungesättigten Ketonen in Gegenwart von Cyclohexylaminacetat und katalytisch erregtem Wasserstoff die Carbonylgruppe aminiert wird, wenn mit einem Überschuß an Cyclohexylamin, also im stark alkalischen Medium gearbeitet wird.The finding was therefore not known and also not to be expected, that with a, ß-unsaturated ketones in the presence of cyclohexylamine acetate and catalytically excited hydrogen the carbonyl group is aminated, if with an excess on cyclohexylamine, i.e. in a strongly alkaline medium.

So wurde z. B. bei der katalytischen Reduktion von Äthylstyrylketon mit überschüssigem Cyclohexylamin i-Phenyl-3-äthyl-3-N-cyclohexylaminopropan und bei der Umsetzung von Benzalaceton mit Cyclohexylamin i-Phenyl-3-methyl-3-N-cyclohexylaminopropan erhalten.So was z. B. in the catalytic reduction of ethyl styryl ketone with excess cyclohexylamine i-phenyl-3-ethyl-3-N-cyclohexylaminopropane and in the reaction of benzalacetone with cyclohexylamine i-phenyl-3-methyl-3-N-cyclohexylaminopropane obtain.

Beispiel i 3z g Äthylstyrylketon ('/1p Mol), Cyclohexylaminacetat und überschüssiges Cyclohexylamin (= 59,4 g Cyclohexylamin [E/1 o Mol] , 12 ccm Eisessig) wurden in 40o ccm Methanol gelöst und mit 9,o g Platin-Bariumsulfat-Katalysator (2g Pt) bei 3,4 atü und Zimmertemperatur hydriert. Nach dem Aufarbeiten zeigte das i-Phenyl-3-äthyl-3-N-cyclohexylaminopropan einen Siedepunkt von Kp12 = 178 bis 17g° und das Hydrochlorid einen Fp. = 144,5 bis i45°- ._ Beispiel 2 Cyclohexylaminacetat und überschüssiges Cyclohexylamin (= 99 g Cyclohexylamin [1 Mol], 30 g Eisessig) wurden in 300 ccm Methanol gelöst, mit 73 g Benzalaceton (1/2 Mol) versetzt und in Gegenwart von 5o g Platin-Bariumsulfat-Katalysator (1o°/oig) katalytisch bei 2o° und 3,4 atü hydriert. Nach Aufnahme der theoretischen Wasserstoffmenge wurde vom Katalysator abfiltriert, der Methylalkohol im Vakuum auf dem Wasserbad abgedampft und der Rückstand mit wäßriger Salzsäure versetzt. Das Hydrochlorid des 1-Phenyl-3-methyl-3-cyclohexylaminopropans zeigt nach dem Umlösen aus Benzol einen Fp. = 16¢ bis 16s°. Die freie Base zeigt einen Kp" = 162 bis 16q.°.Example i 3z g of ethyl styryl ketone (1/1 mol), cyclohexylamine acetate and excess cyclohexylamine (= 59.4 g of cyclohexylamine [E / 10 mol], 12 ccm of glacial acetic acid) were dissolved in 40o ccm of methanol and treated with 9, above-mentioned platinum barium sulfate Catalyst (2g Pt) hydrogenated at 3.4 atmospheres and room temperature. After working up, the i-phenyl-3-ethyl-3-N-cyclohexylaminopropane had a boiling point of bp12 = 178 to 17g ° and the hydrochloride had a melting point = 144.5 to 1445 ° - ._ Example 2 Cyclohexylamine acetate and excess cyclohexylamine ( = 99 g of cyclohexylamine [1 mol], 30 g of glacial acetic acid) were dissolved in 300 cc of methanol, 73 g of benzalacetone (1/2 mol) were added and the mixture was catalytically in the presence of 50 g of platinum-barium sulfate catalyst (10%) Hydrogenated 20 ° and 3.4 atm. After the theoretical amount of hydrogen had been taken up, the catalyst was filtered off, the methyl alcohol was evaporated off in vacuo on a water bath and the residue was treated with aqueous hydrochloric acid. The hydrochloride of 1-phenyl-3-methyl-3-cyclohexylaminopropane has a melting point = 16 ° to 16 ° after redissolving from benzene. The free base shows a b.p. = 162 to 16q. °.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von C3 substituierten 1-Phenyl-3-N-cyclohexylaminopropanen, dadurch gekennzeichnet, daß man a, ß-ungesättigte Ketone der Zusammensetzung C, H" # C H = C H . C O # R, wobei R einen Alkylrest bedeutet, in Gegenwart von Cyclohexylaminacetat und freiem überschüssigem Cyclohexylamin, also bei einem alkalischen pH-Wert, der katalytischen Hydrierung unterwirft.PATENT CLAIM: Process for the production of C3-substituted 1-phenyl-3-N-cyclohexylaminopropanes, characterized in that a, ß-unsaturated ketones of the composition C, H "# C H = C H. C O # R, where R is an alkyl radical, in the presence of cyclohexylamine acetate and free excess cyclohexylamine, i.e. at an alkaline pH value, the subject to catalytic hydrogenation.
DESCH105A 1949-10-15 1949-10-15 Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes Expired DE881041C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH105A DE881041C (en) 1949-10-15 1949-10-15 Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH105A DE881041C (en) 1949-10-15 1949-10-15 Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes

Publications (1)

Publication Number Publication Date
DE881041C true DE881041C (en) 1953-09-14

Family

ID=7422236

Family Applications (1)

Application Number Title Priority Date Filing Date
DESCH105A Expired DE881041C (en) 1949-10-15 1949-10-15 Process for the preparation of C-substituted 1-phenyl-3-N-cyclohexylaminopropanes

Country Status (1)

Country Link
DE (1) DE881041C (en)

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