CH476674A - Process for the preparation of a new amine - Google Patents

Description

  

  



  Process for the preparation of a new amine
The invention relates to a process for the preparation of 9- (γ-methylaminopropyl) -9 1 0-dihydro- -9,1 0-ethano- (1,2) -anthracene of the formula
EMI1.1
 and its salts.



   The new compound has valuable pharmacological properties. In particular, it is psychotropically effective u. mainly shows antidepressant properties. Accordingly, it can be used as a drug.



  But it can also serve as an additive to animal feed. It is also a valuable starting material for the production of other valuable compounds, e.g. the corresponding N, N-disubstituted 9 - (* 1-amino-propyl) - compounds.



   The inventive method for preparing the new compound is characterized in that in a compound of the formula
EMI1.2
 where Z is the group of the formula -CH = N-CH3 or -CH5-N = CH, the CN double bond is reduced to a single bond.



   The reduction can be carried out in a customary manner, using customary reducing agents, primarily metal hydrides, e.g. Dileichtmetallhydriden, such as alkali borohydrides, or of catalytically activated hydrogen, platinum oxide or Raney nickel in particular as catalysts, are carried out.



  The reaction can be carried out in the presence or absence of diluents, condensation and / or catalytic agents, at a reduced, normal or elevated temperature, if appropriate in a closed vessel.



   The starting materials are known or can be obtained by processes known per se.



   The new compound is obtained in free form or in the form of its salts, depending on the reaction conditions and starting materials. The salts of the new compound can be converted into the free compound in a manner known per se, eg. Acid addition salts by reaction with a basic agent. On the other hand, any free base obtained can form salts with inorganic or organic acids. For the preparation of acid addition salts, therapeutically useful acids are used in particular, e.g.

   Hydrohalic acids, for example hydrochloric acid or hydrobromic acid, perchloric acid, nitric acid or thiocyanic acid, sulfuric or phosphoric acids, or organic acids such as formic acid, acetic acid, propionic acid, glycolic acid, lactic acid, pyruvic acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumic acid, citric acid , Ascorbic acid, hydroxymaleic acid, dihydroxymaleic acid, benzoic acid, phenylacetic acid, 4 aminobenzoic acid, 4-hydroxybenzoic acid, anthranilic acid, cinnamic acid, mandelic acid, salicylic acid, 4-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, ethanesulphonic acid, ethanesulphonic acid , p-toluenesulfonic acid, naphthalenesulfonic acid or sulfanilic acid, or methionine, tryptophan, lysine or arginine.

   Mono- or poly-salts can be present here. Salts can also be prepared to purify the free base and converted back into the base.



   A starting material can also be used in the form of a crude reaction mixture obtainable under the reaction conditions, e.g. by reacting 9- (y-amino-propyl) -9, 10-dihydro-9, 10-ethano- (l, 2) -anthracene and formaldehyde.



   The new compound can be used as a medicinal agent in the form of pharmaceutical preparations, which they are in free form or in the form of a salt together with pharmaceutical, organic or inorganic. solid or liquid carriers used for enteral. e.g. oral or parenteral administration are suitable.



   The new compound can also be used in the rearing and feeding of animals in the form of feed or additives for animal feed.



   In the following example the temperatures are given in degrees Celsius.



   example
20 g- [9, 10-dihydro-9, 10-ethano- (1, 2) -9-anthryl] -propionaldehyde are heated to 800 for 5 hours in an autoclave with a saturated solution of methylamine in methanol. The solution is then evaporated in vacuo. The residue is dissolved in 250 ml of ethanol and hydrogenated after adding 4 g of Raney nickel. After the catalyst has been filtered off and the solvent has been evaporated, the residue is treated with 2-n. Hydrochloric acid is added and the mixture is briefly heated to 800. After cooling, the deposited precipitate is recrystallized from isopropanol.

   The 9 - (, - methylaminopropyl) -9, 10-dihydro-9, 10-ethano- (1, 2) -anthracene hydrochloride of the formula is obtained
EMI2.1
 from F. 230-2320
The same product is also obtained by treating 9- (γ-aminopropyl) -9, 10-dihydro-9, 10-ethano- (1,2) -anthracene with formaldehyde and formic acid.



   The p- [9, 10-dihydro- -9,10-ethano- (1.2) -9-anthryl] propionaldehyde used as the starting material can be obtained by Rosenmund reduction of the f3- [9 10-dihydro-9, 10 -ethano- (1, 2) .9.anthryl] .propionic acid chloride can be obtained.

 

Claims (1)

PATENT CLAIM Process for the preparation of the new 9- (γ-methyl aminopropyl) -9, 1 0-dihydro-9, 1 0-ethano- (1 2) -anthrazene of the formula EMI2.2 and its salts, characterized in that in a compound of the formula EMI2.3 where Z is the group of the formula -CH = N-CH3 or CHt-N = Cff, the CN double bond is reduced to a single bond. SUBCLAIMS 1. The method according to claim, characterized in that catalytically reduced. 2. The method according to claim, characterized in that Z represents the CH3-N = CH2 group and that one reduces using Dileichtmetallhydriden. 3. The method according to claim, characterized in that the starting material is used in the form of a crude reaction mixture obtainable under the reaction conditions. 4. The method according to dependent claim 3, characterized in that the starting material in the form of a under the reaction conditions by reacting 9- (y.amino.propyl) .9, 1 0-dihydro-9, 1 0-ethano- (1 2 ) - -anthracene with formaldehyde available crude reaction mixture is used. 5. The method according to claim or one of the dependent claims 1-4, characterized in that the base obtained is converted into its salts. 6. The method according to claim or one of the dependent claims 1-4, characterized in that the salts obtained are converted into the free base.