Chloroacetone → 2-[4-(2-Oxopropyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one

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Reaction Steps

A mixture of 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one (12.4 g), described in Example 2), 1-chloro-2-propanone (5.55 g), potassium carbonate (11.04 g) and acetonitrile (120 ml) was refluxed for 4 hr and filtered. Chloroform and water were added to the filtrate. The organic phase was separated, washed with water, dried and evaporated. The residue was chromatographed on silica gel using methanol-ethyl acetate and the eluates were evaporated to give an oil (6.21 g) of 2-[4-(2-oxopropyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one (VII; R1, R2, R3 and R4 =H and Alk=C--CH2): ir(CHCl3) 3660, 3360, 1720, 1710, 1660 and 1560 cm-1 ; uv max(MeOH) 351 (ε=9310), 255 (ε=13915) and 221 nm(ε=11750); nmr(CDCl3) δ2.12 (s, 3H), 2.62 (t, 4H), 3.21 (s, 2H), 3.35 (s, 4H) and 6.40-7.10 (m, 5H); and Anal. Calcd for C14H18N2O2 : C, 68.26% H, 7.37% N, 11.37% and Found: C, 67.33% H, 7.59% N, 11.44%.

Provenance & Evidence