Abstract
The analgesic drug nefopam reacts in superacidic media to form a dicationic superelectrophiles by ring opening. The dication species is capable of reacting with arenes in Friedel-Crafts-type conversions. This chemistry is used to prepare novel derivatives of nefopam.
Highlights
We reported the ionization of aminoalcohols in superacid to give highly reactive dicationic electrophiles [7]
We report our studies of the acid-catalyzed ring-opening reactions of 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-benzo[ f ] [1, 5] oxazocine and the preparation of novel derivatives of this compound
The superelectrophile from nefopam (3) reacts rapidly with benzene, and the superelectrophile is not formed in appreciable concentration to affect hydride abstraction from the triarylmethane product (15, Scheme 4)
Summary
We reported the ionization of aminoalcohols in superacid to give highly reactive dicationic electrophiles [7]. We report our studies of the acid-catalyzed ring-opening reactions of 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-benzo[ f ] [1, 5] oxazocine (nefopam, a common analgesic drug) and the preparation of novel derivatives of this compound. When nefopam (1) was reacted with several types of arenes in CF3SO3H, the products from electrophilic aromatic substitution were obtained in fair to good yield (Table 1). In the case of product 8, the reaction is best done using 0.1 mmol nefopam HCl, 0.1 mmol benzo-12crown-4, 3 mL CHCl3, and 0.5 mL CF3SO3H.
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