3-Azabicyclo[3,3,1]nonanderivate und Verfahren zu ihrer Herstellung

1,195,746. 3 - Azabicyclo - [3,3,1] - nonanes. YOSHITOMI PHARMACEUTICAL INDUSTRIES Ltd. 14 Aug., 1967, No. 37219/67. Heading C2C. Novel 3-azabicyclo- [3,3,1]-nonanes of formula and their pharmaceutically acceptable acid addition salts, wherein R1 is benzyl, phenethyl, or C 1-4 alkyl; R2 and R3 are each hydrogen or methyl; R4 is hydrogen, C 1- C 4 alkyl, phenyl, tolyl, methoxyphenyl, or trifluoromethylphenyl; R5 is hydrogen, C 1 -C 4 alkanoyl, or C 1 -C 4 alkylsulphonyl; and Z is pyrrolidino, piperidino, morpholino, or 4-methyl-1-piperazino; are prepared (1) when both R4 and R5 are hydrogen, by reducing the corresponding 9- oxo - 3 - azabicyclo - [3,3,1] - nonane; (2) when R5 is hydrogen and R4 is one of the said groups other than hydrogen, by reacting the said 9- oxo-compound with either a Grignard reagent R4MgX (where X is halogen), or a lithium compound R4Li; and (3) when R5 is alkanoyl or alkylsulphonyl, by acylating or sulphonating the corresponding 9-hydroxy-3-azabicyclo-[3,3, - 1]-nonane (i.e. wherein R4 and R5 are hydrogen); the products are then optionally converted to their acid addition salts. The corresponding 9-oxo-3-azabicyclo-[3,3,1]- nonanes are prepared by reacting a tetrahydropyridine derivative, having the groups R1 and Z on the nitrogen and in the 4-position respectively, with an acrolein homologue of formula The oxo-compounds may be converted to their acid addition salts. 1 - Benzyl - 4 - (4 - methyl - 1- piperazinyl) - 1, - 2,3,6-tetrahydropyridine is prepared by reacting 1-benzyl-4-piperidone with 1-methyl-piperazine.