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Oxatomide
Oxatomide (R35443) is a first-generation antihistamine of the phenylpiperazine class. It was discovered at Janssen Pharmaceutica in 1975. Oxatomide lacks any anticholinergic effects. In addition to its H1 receptor antagonism, it also possesses antiserotonergic actions. ==Synthesis==
Reaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group.
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