Methanol → 4-[4-[4-(4-Pyridyl)piperazin-1-yl]phenoxy]butyric acid, hydrochloride salt

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Reaction Steps

A mixture of the product from Example 51 (1.5 g) and methanol (80 ml) was heated to reflux with stirring, and solid pyridine hydrochloride (0.5 g) was added. Heating was stopped and ethyl acetate (10 ml) was added. The reaction mixture was evaporated until a slight turbidity was observed. On further cooling, a precipitate formed which was collected, washed with ethyl acetate and dried to give the title compound (1.33 g) as a beige solid: m.p. >240° C. (dec); NMR (d6DMSO) δ 1.90(2H,m), 2.36(2H,t), 3.17(4H,m), 3.83(4H,m), 3.91(2H,t), 6.89(4H,q), 7.26(2H,d), 8.25(2H,d), 1.21(1H,br), 13.75(1H,br); m/Z 342 (M+H)+ ; calculated for C19H23N3O3. 1.0 HCl: C, 60.4%; H, 6.4%; N, 11.1%; found: C, 60.0%; H, 6.4%, N, 10.8%.

Provenance & Evidence