Chloroacetonitrile → 4-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrile

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Reaction Steps

A mixture of 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one acetate (10.0 g, described in Example 2), chloroacetonitrile (13.2 g) and potassium carbonate (14.5 g) in acetonitrile (110 ml) was stirred at room temperature for 16 hr, and filtered. The filtrate was evaporated. The residue was chromatographed on silica gel (300 g) using ethyl acetate-acetone (4:1) give 1.9 g of the title compound, which was then crystallized from acetone-diethyl ether: mp 133°-135° C.; ir(CHCl3) 2230 and 1565 cm-1 ; uv max(MeOH) 350 (ε=9810), 254 (ε=14575) and 222 nm(ε=11960); nmr(CDCl3) δ2.75 (t, 4H), 3.4 (t, 4H), 3.55 (s, 2H) and 7.0 (m, 5H); and Anal. Calcd for C13H15N3O: C, 68.4% H, 6.56% N, 18.38% and Found: C, 68.15% H, 6.68% N, 18.25%.

Provenance & Evidence