Preparation of asymmetric iminodibenzyl compounds
First Claim
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1. A process for preparing asymmetric iminodibenzyl derivatives, which comprises condensing a 2-nitrobenzyl phosphonic ester of the formula:
- ##SPC5##wherein R is one or more substituents selected from the group consisting of hydrogen, halogen, amino, sulfamoyl, lower alkyl, lower alkoxy and lower alkanoyl, and R2 and R3 are each hydrogen, lower alkyl, phenyl or phenyl (lower) alkyl, provided that when one of R2 and R3 is hydrogen, the other is different from hydrogen, with a 2-nitrobenzaldehyde of the formula;
##SPC6##wherein R1 is one or more substituents selected from the group consisting of hydrogen, halogen, amino, sulfamoyl, lower alkyl, lower alkoxy and lower alkanoyl, R and R1 being asymmetrically attached to the respective positions of the benzene rings when R and R1 are the same or different or being different when R and R1 are attached to the same positions on the respective benzene rings, in an inert organic solvent in the presence of a condensing agent selected from the group consisting of an alkali metal alcoholate, sodium hydride and sodium amide, reducing the resultant 2,2'"'"'-dinitrostilbene of the formula;
##SPC7##wherein R and R1 are each the same as defined above, by catalytic hydrogenation or in the presence of a reducing agent, and ringclosing the resultant 2,2'"'"'-diaminodibenzyl of the formula;
##SPC8##wherein R and R1 are each the same as defined above, by heating in the presence or absence of a catalyst, to give an iminodibenzyl of the formula;
##SPC9##wherein R and R1 are each the same as defined above.
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Abstract
Iminodibenzyl derivatives of the formula: ##SPC1##
Wherein R and R1 each represent hydrogen, halogen, amino, sulfamoyl, lower alkyl, lower alkoxy or lower alkanoyl, provided that R and R1 can not both be hydrogen and when R and R1 are the same, they are located at positions asymmetric to each other, are produced in high purity and yield by a series of reactions which proceed through novel 2,2'"'"'-dinitrostilbene or 2,2'"'"'-diaminostilbene and 2,2'"'"'-diaminodibenzyl derivatives. The reaction sequence involves condensation, reduction and ring-closure reactions to give asymmetric as well as symmetric iminodibenzyl derivatives. The resulting iminodibenzyl derivatives may be converted to useful pharmaceutical compounds having anti-depressant, analgesic or anti-allergic properties.
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8 Claims
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1. A process for preparing asymmetric iminodibenzyl derivatives, which comprises condensing a 2-nitrobenzyl phosphonic ester of the formula:
- ##SPC5##
wherein R is one or more substituents selected from the group consisting of hydrogen, halogen, amino, sulfamoyl, lower alkyl, lower alkoxy and lower alkanoyl, and R2 and R3 are each hydrogen, lower alkyl, phenyl or phenyl (lower) alkyl, provided that when one of R2 and R3 is hydrogen, the other is different from hydrogen, with a 2-nitrobenzaldehyde of the formula;
##SPC6##wherein R1 is one or more substituents selected from the group consisting of hydrogen, halogen, amino, sulfamoyl, lower alkyl, lower alkoxy and lower alkanoyl, R and R1 being asymmetrically attached to the respective positions of the benzene rings when R and R1 are the same or different or being different when R and R1 are attached to the same positions on the respective benzene rings, in an inert organic solvent in the presence of a condensing agent selected from the group consisting of an alkali metal alcoholate, sodium hydride and sodium amide, reducing the resultant 2,2'"'"'-dinitrostilbene of the formula;
##SPC7##wherein R and R1 are each the same as defined above, by catalytic hydrogenation or in the presence of a reducing agent, and ringclosing the resultant 2,2'"'"'-diaminodibenzyl of the formula;
##SPC8##wherein R and R1 are each the same as defined above, by heating in the presence or absence of a catalyst, to give an iminodibenzyl of the formula;
##SPC9##wherein R and R1 are each the same as defined above. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
- ##SPC5##
Specification
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Current AssigneeEiichi Kitamura, Tameo Kitamura, Tetsuo Kitamura
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Original AssigneeEiichi Kitamura, Tameo Kitamura, Tetsuo Kitamura
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InventorsKitamura, Tetsuo, Kitamura, Ryoichi, Kitamura, Eiichi, Kitamura, Tameo
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Primary Examiner(s)Rollins, Alton D.
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Application NumberUS05/382,120Time in Patent Office1,337 DaysField of Search260/239 DUS Class Current540/588CPC Class CodesC07D 223/22 Dibenz [b, f] azepines; Hyd...
