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

HRID 1454403Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=2[CH:16]=[C:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CO>[N:11]1([C:14]2[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=2[CH2:16][CH:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

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)+.

Workup

filtrationThe mixture was filtered through Celite™, fresh 10% palladium on carbon
additionwas added (2.0 g)
temperaturewas heated at 60° C. for 7 hours
filtrationThe mixture was filtered through Celite™
customthe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography (20:1 chloroform-methanol w/1% ammonium hydroxide)

Sources & evidence

ORD record: ord-eba59133ed2c4725b6679018c4483d16
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479559B2

Reaction notes

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