Acetic Acid → HCID 178468707, compound

Participants

Reaction Steps

To a solution of the above-prepared 1-(2-phenyl-4-piperidin-1-yl-thiazol-5-yl)-ethanone (0.545 mmol) in dry THF (5 mL) was treated dropwise with a 1.0M potassium t-butoxide in THF solution (0.654 mmol). The suspension was stirred at room temperature under nitrogen for 15 minutes. Diethyl oxalate (0.600 mmol) was added, and the brown suspension was diluted with additional THF (6 mL) and allowed to stir at room temperature for 30 minutes. The reaction mixture was quenched by adding glacial acetic acid (0.710 mmol) and ethanol (5 mL). The solvent was removed in vacuo leaving a residual oil that was dissolved in absolute EtOH (5 mL). The ethanolic solution was treated with hydrazine monohydrate(0.655 mmol) and the mixture heated at 80° C. for 1 hour. The resulting yellow suspension was concentrated in vacuo leaving a residual oil that was dissolved in ethyl acetate. This organic phase was washed with water, saturated NaHCO3 and brine, then dried over MgSO4 and evaporated in vacuo to give a yellow oily solid. Silica gel chromatography provided the title compound (59%) as a yellow solid. 1H NMR(CDCl3): δ 1.4 (t, 3H), 1.6-1.9 (6H), 3.1 (m, 4H), 4.4 (q, 2H), 6.9 (broad s, 1H), 7.4-7.5 (m, 3H), 7.9 (m, 2H).

Provenance & Evidence