Pyrrolo[2,1‐<i>c</i>][1,4]benzoxazepines. <b>2</b>. Synthesis of 5‐phenyl derivatives

Abstract

Abstract A series of 5‐phenylpyrrolo[2,1‐ c ][1,4]benzoxazepines with basic substituents at the 11‐position has been synthesized utilizing a nucleophilic aromatic fluoride displacement‐cyclization. Piperidinyl derivatives were prepared by Vilsmeier formylation of the key 1‐[(2‐fluorophenyl)phenylmethyl]pyrrole ( 4 ) followed by addition of a piperidinyl Grignard reagent and cyclization of the resulting carbinol. A (dimethylamino)methyl derivative was prepared via an analogous cyclization of α‐(dimethylamino)methyl‐1‐[(2‐fluorophenyl)phenyl‐methyl]‐1 H ‐pyrrole‐2‐methanol ( 10 ), obtained by the Hoeben‐Hoesch acylation of 4 with chloroacetonitrile, addition of dimethylamine to the resulting α‐chloroketone 8 , and reduction of the α‐(dimethylamino)ketone 9 with sodium borohydride to give 10 .