HCID 54455304, compound → HCID 67143148, compound

HRID 1454401Notes

Reaction equation

HRID 1454401 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[C:6]([CH:14]=1)[CH:7]=[C:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13]>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)=[C:6]([CH:14]=1)[CH2:7][CH:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13]

Participants

4

Reactant 1

HCID 54455304HCID 54455304, compound

Product 1

HCID 67143148HCID 67143148, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3.9 g (13.5 mmol) of 3-[5-Fluoro-2-(4-methyl-piperazin-1-yl)-benzylidene]-pyrrolidin-2-one in 150 mL of methanol is added 1.0 g of Pd/C. Hydrogenation at 50 psi with heating to 50° C. was complete after 24 hours. The reaction was filtered over Celite™ using methanol and concentrated. The resultant residue was purified by silica gel chromatography to provide 3.8 g (98% yield) of 3-[5-Fluoro-2-(4-methyl-piperazin-1-yl)-benzyl]-pyrrolidin-2-one. Diagnostic C13 NMR (100 MHz, CDCl3) 27.3, 31.7, 40.5, 42.1, 46.2, 53.0, 55.8, 113.7, 113.9, 116.6, 116.8, 122.3, 122.4, 137.9, 148.0, 161.0; MS m/z 292.2 (M+1).

Workup

  1. filtrationThe reaction was filtered over Celite™
  2. concentrationconcentrated
  3. customThe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-07b35dcb49af445eb450e6e3f85ff68e
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

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