Acetic Acid → Ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate

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Reaction Steps

[A] Synthesis of 1-benzyl-piperidin-4-ylidene)-cyanoacetate (2; FIG. 4). A solution of 1-benzyl-piperidin-4-one (75.1 g, 0.40 mol) in toluene (9400 mL), ethyl cyanoacetate (50.6 mL, 0.48 mol) and acetic acid (918.2 mL, 0.32 mol) was refluxed for 4 hr. The mixture was quenched with ice-water and extracted with diethyl ether. The combined extracts were washed with water, brine and dried over Na2SO4 to give ethyl (1-benzyl-piperidin-4-ylidene)cyanoacetate in quantitative yield. Rf=0.53 (hexane:AcOEt=1:1).

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