Carbinoxamine is a histamine antagonist, specifi cally an

Chapter 21, Problem 21.53

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Carbinoxamine is a histamine antagonist, specifi cally an H1-antagonist. The maleic acid salt of the levorotatory isomer is sold as the prescription drug Rotoxamine. Br N 1 1 Me Me Me Cl N O N Cl Cl N Me CHO Carbinoxamine (a) Propose a synthesis of carbinoxamine. (Note: Aryl bromides form Grignard reagents much more readily than do aryl chlorides.) (b) Is carbinoxamine chiral? If so how many stereoisomers are possible? Which of the possible stereoisomers are formed in this synthesis?

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