CH467744A - Process for the preparation of 5H-dibenzo- (a, d) -cycloheptenes - Google Patents

Description

  

  
 



  Process for the preparation of 5H-dibenzo- (1, d) -cycloheptenes
The present invention relates to a process for the preparation of new 5H-dibenzo- (a, d) - cycloheptenes and their salts, which are substituted on the carbon atom of the 5-position by an aminopropylidene radical.



   These compounds can be used to treat mental illnesses because they are effective as an antidepressant agent or to cheer up the mind and as a psychic energizer. In such cases, the daily dose can be 5 to 250 mlg, which is preferably taken in divided doses. These compounds are preferably administered in the form of their salts obtainable with acids.



   The compounds which can be prepared by the process according to the invention have the following formula:
EMI1.1
 wherein X and X 'are hydrogen; an alkyl group or an alkenyl group of up to 6 carbon atoms; a perfluoroalkyl group of up to 4 carbon atoms; a phenyl or substituted phenyl radical, an acyl group or a perfluoroacyl group of up to 4 carbon atoms; an amino group, an alkylamino group of up to 4 carbon atoms; a dialkylamino group of up to 6 carbon atoms; an acylamino group or a perfluoroacylamino group or an alkylsulfonylamino group with up to 4 carbon atoms; Halogen;

   Hydroxyl; an alkoxy group or a nonperfluoro group. alkoxy group, with Es to 4 carbon atoms; Cyan; Carboxy; Carbamyl; an alkylcarbamyl group of up to 5 carbon atoms; a dialkylcarbamyl group with ibis of 9 carbon atoms; a carbalkoxy group of up to 6 carbon atoms; Mercapto or an alkyl mercapto group or an alkylsulfonyl group or a perfluoroalkylsulfonyl group with up to 4 carbon atoms;

   Sulfamyl; an alkyl isulfamyl group with up to 4 carbon atoms or a dialkylsulfamyl group with up to 6 carbon atoms and R and R 'are hydrogen; an alkyl, alkenyl, alkoxy or cycloalkyl group each having up to 6 carbon atoms; Phenyl; substituted phenyl or aralkyl, e.g. B. benzyl.



     The process according to the invention now relates to the conversion of a corresponding primary amine into the secondary amine of the formula mentioned, and is characterized in that a primary amil of the formula
EMI1.2
 with a ketone or an aldehyde in a solvent at reflux temperature to form a compound of the formula
EMI1.3
 brings this compound to reaction in the presence of a palladium catalyst to the secondary amine of the formula
EMI2.1
 hydrogenated.



     The product obtained can easily be converted into the corresponding salts.



   The reaction with the ketone or aldehyde is preferably carried out in benzene or toluene as the solvent, with the mixture being heated to reflux, whereupon the hydrogenation takes place in the presence of a palladium catalyst.



   This process for converting the primary into the secondary amine is particularly advantageous when larger groups than methyl groups are introduced.



   The production of the starting material is described in Swiss Patent No. 464 893.



   Example 1 S- (3-butylaminopropylidene) -5H-dibenzo- (a, d) -cycloheptene
Butyraldehyde is added to a solution of 5- (3-aminopropylidene) -5H-dibenzo- (a, d) -cycloheptene in benzene and the mixture is heated to reflux with continuous separation of water until the latter has ended. After the benzene has evaporated, the 5- (3-butylideneaminopropylidene) -5H-dibenzo- (a, d) cycloheptene formed is distilled under reduced pressure, dissolved in absolute alcohol and hydrogenated in the presence of a platinum catalyst. After the catalyst has been filtered off and the solvent has been distilled off, the product is purified by distillation under reduced pressure.



   Example 2
A solution of 5- (3-aminopropylidene) -5H-dibenzo- (a, d) -cycloheptene and excess acetone from this in ethanol is hydrogenated and separated according to the method of Example 1. The product obtained is 5- (3-isopropylaminopropylidene ) -5H-dibenzo (a, d) -cycloheptene.

 

Claims (1)

PATENT CLAIM Process for the preparation of 5H-dibenzo- (a, d) - cycloheptenes of the formula EMI2.2 or their salts, in which X and X 'are hydrogen; an alkyl group or an alkenyl group of up to 6 carbon atoms; a pertluoroalkyl group of up to 4 carbon atoms; a phenyl or substituted phenyl radical, an acyl group or a perfluoroacyl group with up to 4 carbon atoms; an amino group, an alkylamino group with up to 4 carbon atoms; a dialkylamino group of up to 6 carbon atoms; an acylamino group or a perfluoroacylamino group or an alkylsulfonylamino group having up to 4 carbon atoms; Halogen; Hydroxyl; an alkoxy group or a perfluoroalkoxy group having up to 4 carbon atoms; Cyan; Carboxy; Carbamyl; an alkylcarbamyl group of up to 5 carbon atoms; a dialkylcarbamyl group of up to 9 carbon atoms; a carbalkoxy group of up to 6 carbon atoms; an IMercapto or an alkyl meleapto group or an alkylsulfonyl group or a perfluoroalkylsulfonyl group with up to 4 carbon atoms; sulfamyl; an alkylsulfamyl group with up to 4 carbon atoms or a dialkylsulfamyl group with up to 6 carbon atoms and R and R 'are hydrogen; an alkyl, alkenyl, alkoxy or cycloalkyl group each having up to 6 carbon atoms; Phenyl; substituted phenyl or aralkyl, characterized in that a primary amine of the formula EMI2.3 with a ketone or an aldehyde in a solvent at reflux temperature to form a compound of the formula EMI2.4 reacts and hydrogenates this compound in the presence of a palladium catalyst.