Propynamide → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

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Reaction Steps

To a solution of 1-benzyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (2.58 g, 10.65 mmol) in toluene (30 mL) is added propiolamide (1.47 g, 21.29 mmol) and the mixture is refluxed for 4 hr. The mixture is cooled to rt and the solvent is removed in vacuo. The residue is partitioned between NaHCO3 (30 mL) and DCM (30 mL). The layers are separated and the aqueous layer is extracted with DCM (30 ml). The combined extracts are dried and evaporated and the residue is purified by flash column with 5% MeOH in DCM to give the title compound as a light yellow solid. MS (M+1): 241.1.

Provenance & Evidence