Patent GB-1081124-A (GB)
Title: Diimides of substituted naphthalene tetracarboxylic acids
Inventor: SCHUTZ SIEGISMUND
Filed: 1965-06-04
Abstract: Novel compounds of the Formula I, wherein A represents a direct bond or a branched or straight C1- 6 alkylene chain which may be substituted by hydroxy groups; R represents a hydrogen atom or a C2- 8 unsaturated aliphatic-radical which can be substituted by polycyclic, heterocyclic or unsaturated cycloalkyl radicals and which can be interrupted by an oxygen atom or an imino radical (that latter being optionally substituted by an alkyl radical or by an unsubstituted or halogen, alkyl or alkoxy substituted cycloalkyl, aryl, aralkyl or polycyclic radical) or represents a branched or straight, saturated or unsaturated C9- 20 aliphatic hydrocarbon radical (which may be interrupted by oxygen atoms and/or substituted by hydroxyl groups) or an aryloxyalkyl radical or a C1- 6 alkyl radical linked to R1 to form a ring substituted by saturated aliphatic radicals; R1 represents a hydrogen atom or a branched or straight chain unsaturated C2- 8 aliphatic radical (which can be substituted by polycyclic, heterocyclic and unsaturated cycloaliphatic hydrocarbon radicals), which can be interrupted by an oxygen atom or an imino group (which imino may be substituted by an alkyl radical or by an optionally halogen, alkyl, alkoxy, amino or nitro substituted cycloalkyl, aryl, aralkyl or polycyclic radical) or a branched or straight chain saturated or unsaturated C9- 20 aliphatic radical (which may be interrupted by oxygen atoms and/or substituted by hydroxyl groups) or an aryloxyalkyl radical; and R2 represents a hydrogen atom or a C1- 4 alkyl radical; and acid addition salts thereof, are prepared by reacting naphthalene - (1,4,5,8) - tetracarboxylic acid or its bis-anhydride with an amine of the formula NH2.CHR2.A.NRR1; by reacting a halide of the Formula II with an amine of the formula R-NH-R1 or by reducing a nitrile of the Formula III, wherein D represents a direct linkage or a C1- 5 alkylene chain.  <FORM:1081124/C2/1> <FORM:1081124/C2/2> <FORM:1081124/C2/3> g  - (4 - Methylpiperidino) propylamine, N - methyl - N - cyclohexyltrimethylene diamine, g -(2 - methylpiperidino) - propylamine, N-(2-methylcyclohexyl) trimethylene - 1,3 - diamine, g  - (2 - ethylpiperidino) propylamine, g  - [N-methyl - N - (b  - ethoxyethyl) amino] propylamine, g  - octadecylaminopropylamine, g  - (N - ethyl-N-cyclohexylamino) propylamine and g  - (3,3,4,4 - tetramethylpyrrolidino) propylamine may be prepared by reacting the appropriate amine with acrylonitrile and catalytically reducing the resultant propionitrile. 3,3,4,4-Tetramethylpyrrolidine may be prepared by reducing tetramethylsuccinimide or hydrogenating tetramethylsuccinic acid dinitrile.  b  - Hydroxy - g  - (N - ethyl - N - p - chloro-phenylamino)-propylamine may be prepared by reacting p-chloro-N-ethylaniline with epichlorohydrin and reacting the product with ammonia.  b  - Bicyclo[2,2,1]hept - 2 - ylmethylaminoethyl-amine may be prepared by condensing 2,5-endomethylene - D 3 - tetrahydrobenzaldehyde with ethylene diamine and catalytically hydrogenating the product.  N - (2 - Methyl - prop - 2 - enyl) ethylene diamine may be prepared by reacting 1-chloro-(2-methylpropene-2) with ethylene diamine.  N - (2 - Chlorobenzyl) ethylene diamine may be prepared by reacting 2-chlorobenzyl chloride with ethylene diamine.  N - (b  - Pyrrolidinoethyl) ethylene diamine may be prepared by reacting b -pyrrolidinoethyl chloride with ethylene diamine.