IL44291A - Preparation of 2-aminoindane derivatives - Google Patents

Description

of 2 This invention relates to a process for preparing derivatives of of the formula n is equal to 2 or the group having a or branched and represent a lower radical containing 1 to 3 carbon whereby and may also form together with atom a saturated A is phenyl optionally substituted with one or more lower alkoxy or halogen groups in the meta para position of the phenyl radical and B represents an group of the or different represent a lower a kyl or ydroxyalky radica whereby may also represent whereas and may also form with the attached nitrogen atom a nitrogenous saturated heterocyclic optionally containing a further hetero which may be substituted with lower as well as the acid addition salts of said The compounds of formula are useful for the treatment of heart According to French Patent 2 081 there is known a process for preparing or by reacting aminoindane with sodium amide to form a sodium salt of the which sodium salt is then reacted with a chlorinated According to this the compounds of mula are prepared by a method comprising the two wing steps with a of the formula CI so as to obtain an intermediate a This intermediate product may be isolated or without isolation in the following Reaction of formula with an amine of the following formula In the above formulae to A and B have the above EXAMPLE 1 Preparation of hydrochloride I A mixture of 10 g of and of 25ml of is heated at during 24 After cooling to 5ml of benzene are added and the ture is The residue is dissolved in 50ml of lamine and 70 ml of After addition of of sodium the mixture is refluxed during 24 After tration to the obtained residue is treated with the obtained solution is made alkaline by means of ammonia and extracted with The organic solution is then treated with water and acidified to a pH of After extraction with dichloromethane the aqueous phase is concentrated to dryness and the residue is recrystallized f om methanol of dih drochloride meltin at obtained solution adjusted to a pH of it is possible to recover of the desired 120 EXAMPLES 2 to The compounds of the formula in which and have the meanings indicated in the following table have been prepared by the method described in example 1 using the appropriate of formula and the appropriate amine of formula instead of and diethylamine TABLE A B n R2 of acid addition salt 2 phenyl H ride 3 H 3 xyphenyl de 1 mole 4 H 3 oxalate phenyl 125 128 5 H 3 ride phenyl 6 H 3 phenyl fumarate 138 140 7 phenyl H 3 ride 8 8 phenyl H 4 ride 9 phenyl H 2 C2H5 ride 10 phenyl H 2 CH5 ride insufficientOCRQuality

Claims (1)

1. 44291/2 The embodiment of the invention in v/hich an exclusive property or privilege is claimed are defined as follows : C L A I M S 1.- A process for preparing derivatives of 2-aminoindane of the formula : wherein a straight or branched chain, R1 and R2 represent a lov/er alkyl radical containing 1 to 3 carbon atoms, whereby and R2 may also form together with the adjacent nitrogen atom a nitroge- saturated nous/heterocyclic ring, A is phenyl optionally substituted with one or more hydroxy, lower alkoxy or halogen groups in the ortho, meta and/or para position of the phenyl radical and B represents hydrogen, an alkoxy radical containing 1 to 3 carbon atoms or a group of the formula in which R, and R^, which may be identical or different represent a lower alkyl or hydroxyalkyl radical, whereby R^ may also represent hydrogen, whereas R^ and R^ may also form with the attached nitrogen atom a nitrogenous saturated heterocyclic ring, optionally containing a further hetero atom, which may be substituted with lower alkyl, as well as the acid addition salts of said compound said process comprising the two following steps : ■ - reaction of a N-phenyl-2-arainoindane of the formu with a bromo-chloroalkane of the formula Br-(CH2)n-Cl ' (H ) so as to obtain an intermediate product, i.e. a N-phenyl-N- - reaction of the N-phenyl-N-chloroalkyl=2-aminoin= dane of formula (IV) with an amine of the following formula n, R1 , A and B having the above meanings in the formula (II), (III), (IV) and (V) , the obtained compound of formula I being converted into an acid addition salt, if desired. 2.- A process according to claim 1, in which the. compound of formula (IV) is isolated before the reaction thereof with amine of formula (V).