Process for the preparation of 2-aminoindane derivatives

Details Process for the preparation of 2-aminoindane derivatives Process for the preparation of 2-aminoindane derivatives

C - Chemistry, Metallurgy

07

D

260/392.6, 260/5

C07D 295/12 (2006.01) C07D 295/13 (2006.01)

Patent

CA 1068289

ABSTRACT OF THE DISCLOSURE Preparing derivatives of 2-aminoindane of formula: Image (I) in which n = 2, 3 or 4, the (CH2)n group having a straight or branched chain, R1 represents a hydrogen atom, an alkyl or hydroxy- alkyl group having 1 to 3 carbon atoms or an alkenyl or alkynyl group having 2 or 3 carbon atoms, R2 represents an alkyl or hydroxyalkyl group having 1 to 3 carbon atoms or an alkenyl or alkynyl group having 2 or 3 carbon atoms, whereby R1 and R2 may be identical or different and may form together with the contiguous nitrogen atom a nitrogenous heterocyclic group, R3 represents a hydrogen atom or a substituent, such as a hydroxy, chloro, tri- fluormethyl or lower alkyl radical, which may be in the ortho, meta or para position of the phenyl group and R4 represents a hydrogen atom, an alkoxy radical having 1 to 3 carbon atoms or a dialkylamino group, as well as the acid addition salts of the 2- aminoindane derivatives of formula (I). ??is is made possible by reacting a N-phenyl-2-aminoindane of formula: (II) Image in which R3 and R4 have the meanings given above, with sodamide (NaNH2) and an halogenated amine of formula: Image (III) in which n, R1 and R2 have the meanings given above. A mixture of sodamide and an organic solvent, such as benzene or toluene, heated to reflux temperature, is reacted with N-phenyl-2-aminoindane of formula (II), possibly in the form of its hydrochloride, and after the emission of ammonia has ended, always keeping the mixture at reflux temperature, the halogenated amine of formula (III) is added in the form of its hydrochloride. The amount of sodamide (NaNH2) is sufficient not only for the formation of the sodium salt of the N-phenyl-2-aminoindane of formula (II) as an inter- mediate compound, but also to release the free base from the hydro- chloride of the N-phenyl-2-aminoindane of formula (II) and/or the hydrochloride of the halogenated amine of formula (III).

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