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

HRID 710021Notes

Reaction equation

HRID 710021 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH2:24][CH2:23]1)[C:7]([NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])=[O:8])([O-])=O>C(O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH2:24][CH2:23]1)[C:7]([NH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])=[O:8]

Participants

4

Reactant 1

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

Product 1

HCID 866758943-amino-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamideYield 50.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

3-Nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide (1.5 g, 3.2 mmol) was taken in a mixture of ethanol/methanol (50.0 mL/20.0 mL). This was added to a flask containing Pd/C (5 wt %) (0.15 g). The solution was evacuated and nitrogen purged and stirred under a balloon of hydrogen for 8 h. LC-MS indicated completion of reaction. Reaction was stopped, evacuated and nitrogen purged and filtered on celite. The solvent was rotavaped out to give 3-amino-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide (0.7 g, 47%).

Workup

  1. additionThis was added to a flask
  2. customThe solution was evacuated
  3. customnitrogen purged
  4. customcompletion of reaction
  5. customReaction
  6. customevacuated
  7. customnitrogen purged
  8. filtrationfiltered on celite

Sources & evidence

ORD record
ord-152417ca967842db9781af193c909953
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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