Verfahren zur Herstellung von 2-(3-Pyrrolidinyl)-isoindolinen

1,256,931. 2 - (3 - Pyrrolidinyl) - isoindolines. A. H. ROBINS CO., Inc. 21 March, 1969 [29 March, 1968], No. 14986/69. Heading C2C. Novel 2 - (3 - pyrrolidinyl) - isoindolines of the general formula wherein R is a hydrogen atom or a C 1-8 alkyl, #-hydroxy-C 1-8 alkyl, phenyl, phenyl-C 1-8 alkyl, cycloalkyl, N - C 1-8 alkyl - carbamoyl, N- phenyl - carbamoyl, N - (substituted phenyl)- carbamoyl, halophenoxyacyl, N,N - diphenylcarbamoyl, N,N - di - (substituted phenyl)- carbamoyl, carbamoyl or amidino group, R1 is a hydrogen atom or a methyl group, R2 is a hydrogen, fluorine, chlorine or bromine atom, or a trifluoromethyl, C 1-8 alkyl or C 1-8 alkoxy group, Y is an alkyleneoxy group, z is 0 or 1, m is 0, 1, 2 or 3 and n is 0, 1, 2, 3 or 4, and acid addition salts thereof are prepared (a) when R is a hydrogen atom or a C 1-8 alkyl, phenyl, phenyl-C 1-8 alkyl or cycloalkyl group and z is 0, by reduction of the corresponding N-(3-pyrrolidinyl)-phthalimide with lithium aluminium hydride; (6) when R is a hydrogen atom and z is 0, by hydrogenolysis of the corresponding 2- (3 - pyrrolidinyl) - isoindoline of the above general formula, wherein R is a benzyl group and z is 0; (c) when R is a phenyl-C 1-8 alkyl or #-hydroxy-alkyl group and z is 0, by reaction of the corresponding 2-(3-pyrrolidinyl)-isoindoline of the above general formula, wherein R is a hydrogen atom and z is 0 with a phenyl-C 1-8 alkyl halide or a halo-C 1-8 alkanol; (d) when R is an N-C 1-8 alkyl-carbamoyl, N-phenyl-carbamoyl or N - (substituted phenyl) - carbamoyl group and z is 1, by reaction of the product of process (c) above, wherein R is an #-hydroxyalkyl group with a C 1-8 alkyl isocyanate, phenyl isocyanate or a substituted phenyl isocyanate; (e) when R is an N-alkyl-carbamoyl, N-phenylcarbamoyl or N - (substituted phenyl) - carbamoyl group and z is 0, by reaction of the corresponding 2 - (3 - ,- pyrrolidinyl) - isoindoline of the above general formula, wherein R is a hydrogen atom with a C 1-8 alkyl isocyanate, phenyl isocyanate or a substituted phenyl isocyanate ; (f) when R is a carbamoyl group and z is 0, by reaction of the corresponding 2-(3- pyrrolidinyl)-isoindoline of the above general formula wherein R is a hydrogen atom with nitrourea; (g) when R is a N,N-diphenylcarbamoyl group and z is 0, by reaction of the corresponding 2 - (3 - pyrrolidinyl) - isoindoline of the above general formula, wherein R is a hydrogen atom with diphenylcarbamoyl chloride; (h) when R is an amidino group