Ammonium formate → 3-{[2-(4-Methylpiperazin-1-yl)phenyl]methyl}pyrrolidin-2-one

HRID 1454402Notes

Reaction equation

HRID 1454402 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[CH:10]=[C:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[CH2:10][CH:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54222857HCID 54222857, compound

Product 1

HCID 159842013-{[2-(4-Methylpiperazin-1-yl)phenyl]methyl}pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A round bottom flask under N2 was charged with 10% Pd/C (0.99 g) and ethyl alcohol (50 mL) followed by 3-[2-(4-methylpiperazin-1-yl)-benzylidene]-pyrrolidin-2-one (3.00 g, 11.1 mmol) and ammonium formate (6.97 g, 110.6 mmol). The reaction mixture was stirred at room temperature for 1 hour then heated to 50° C. for 3 hours. The reaction mixture was cooled to room temperature and filtered through Celite™ under N2. The Celite™ pad was washed with ethyl alcohol (25 mL) and water (10 mL). The filtrate was evaporated to give white solids which were partitioned between ethyl acetate (25 mL) and H2O (10 mL). The aqueous layer was extracted with additional ethyl acetate (2×25 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to a white solid (2.90 g, 96%). The material could be used crude or triturated with ethyl acetate (5 vol) to give 80% recovery of improved purity of the title compound. 13C NMR (100 MHz, CDCl3) d 180.6, 152.1, 135.5, 130.4, 127.5, 124.5, 120.8, 55.9, 52.9, 46.4, 42.4, 40.6, 31.8, 27.3; MS (AP/Cl) 274.3 (M+H)+.

Workup

  1. temperaturethen heated to 50° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite™ under N2
  4. washThe Celite™ pad was washed with ethyl alcohol (25 mL) and water (10 mL)
  5. customThe filtrate was evaporated
  6. customto give white solids which
  7. customwere partitioned between ethyl acetate (25 mL) and H2O (10 mL)
  8. extractionThe aqueous layer was extracted with additional ethyl acetate (2×25 mL)
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated to a white solid (2.90 g, 96%)
  12. customtriturated with ethyl acetate (5 vol)

Sources & evidence

ORD record
ord-fa59647b3a68460f88e248ec3a698834
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

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