Ammonium Hydroxide → 4-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetamide

Participants

Reaction Steps

A solution of 4-(2-oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrile (3.0 g; described in Example 3) in conc. sulfuric acid (30 ml) was allowed to stay at room temperature for 3 days. The reaction mixture was poured over ice and conc. ammonium hydroxide slowly while stirring, then extracted with chloroform. Evaporation of the solvent left 2.7 g crude product, which was recrystallized from methanol to yield 2.2 g of the title compound: mp 169°-171° C.; ir(CHCl3) 3500, 3430, 3370, 1685 and 1563 cm-1 ; uv max(MeOH) 351 (ε=9920), 254 (ε=14810) and 221 nm(ε=12090); nmr(CDCl3)δ2.75 (t, 4H), 3.09 (s, 2H), 3.35 (t, 4H), 6.00 (2H) and 6.8 (m, 5H); and Anal. Calcd for C13H17N3O2 : C, 63.14% H, 6.93% N, 16.99% and Found: C, 63.24% H, 7.00% N, 16.99%.

Provenance & Evidence