Potassium Carbonate → 3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide

HRID 710020Notes

Reaction equation

HRID 710020 reaction equation
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[O:7])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[C:29]1([CH3:41])[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>CN(C=O)C>[N+:20]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:2]=1[N:38]1[CH2:39][CH2:40][N:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH3:41])[CH2:36][CH2:37]1)[C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])=[O:7])([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 919652-MeppHCID 712246724-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide

Product 1

HCID 712248173-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-Fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide (2.0 g, 6.47 mmol) in DMF (10 mL), K2CO3 (1.7 g, 12.94 mmol) was added followed by 1-o-tolyl-piperazine (1.7 g, 9.7 mmol), and the reaction mixture was stirred at room temperature for 16 h. DMF (2.0 mL) was added and filtered. The solid was washed with MeOH (300 mL) and methanol layer was evaporated to give the acid 3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide in the first crop (1.8 g, 62%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with MeOH (300 mL) and methanol layer
  3. customwas evaporated

Sources & evidence

ORD record
ord-5685e88cfe8b44a7a0a7238c32cc46e6
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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