Methyl 3-[4-(4-nitrophenyl)piperazinyl]propanoate → Methyl 3-[4-(4-aminophenyl)piperazin-1-yl]propanoate

HRID 2353225Notes

Reaction equation

HRID 2353225 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 16450139Methyl 3-[4-(4-nitrophenyl)piperazinyl]propanoate

Product 1

HCID 58902522Methyl 3-[4-(4-aminophenyl)piperazin-1-yl]propanoateYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the compound from step 1 (1.8 g), Pd/C (5%, 0.3 g) and ethanol (150 ml) was stirred at ambient temperature under hydrogen (1 atm) for 16 h. The reaction mixture was filtered and the solvent was removed under vacuum to furnish the title compound as a light tan solid (1.52 g, 94.6%): MS (ESI) m/z 264 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.55 (t, J=7.2 Hz, 2H), 2.65 (t, J=4.8 Hz, 4H), 2.77 (t, J=7.2 Hz, 2H), 3.05 (br, 4H), 3.70 (s, 3H), 6.80-6.83 (m, 2H), 8.11-8.14 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4103a7928c5745c4be595e2286662459
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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