3-[2-(4-Benzyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one → 3-(2-Piperazin-1-yl-benzyl)-pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-[2-(4-benzyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one (Preparation 15, 6.3 g, 18 mmol) and 10% palladium on carbon (1.5 g) in methanol (100 mL) was placed under a hydrogen atmosphere (50 psi) and was heated at 50° C. for 24 hours. The mixture was filtered through Celite™, fresh 10% palladium on carbon was added (2.0 g), and the mixture was placed under hydrogen (50 psi) and was heated at 60° C. for 7 hours. The mixture was filtered through Celite™, the solvent was removed in vacuo and the residue was purified by silica gel chromatography (20:1 chloroform-methanol w/1% ammonium hydroxide) to give 3.8 g (82% yield) of the title compound. 13C NMR (100 MHz, CDCl3) 180.7, 152.6, 135.5, 130.4, 127.5, 124.5, 120.8, 54.3, 46.8, 42.4, 40.7, 31.9, 27.3; MS (AP/Cl) 260.1 (M+H)+.

Provenance & Evidence