Succinic anhydride → 4-Oxo-4-[4-[4-(4-pyridyl)piperazin-1-yl]phenyl]aminobutyric acid

HRID 1290535Notes

Reaction equation

HRID 1290535 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1>CN(C=O)C>[O:26]=[C:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1)[CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 108904611-(4-Aminophenyl)-4-(4-pyridyl)piperazine

Product 1

HCID 189182414-Oxo-4-[4-[4-(4-pyridyl)piperazin-1-yl]phenyl]aminobutyric acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-aminophenyl)-4-(4-pyridyl)piperazine (100 mg) in DMF (8ml) was added succinic anhydride (79 mg). The reaction mixture was stirred at room temperature for 2.5 hr and a precipitate was collected, washed with DMF and ethanol, then dried to give the title compound (106 mg) as a beige-coloured solid: m.p. 263°-264° C.; NMR (d6DMSO+CF3CO2H) δ 2.68(4H,m), 3.80(4H,m, 4.19(4H,m), 7.20(2H,d), 7.56(2H,d), 7.82(2H,d), 8.21(2H,d), 9.62(1H,s); m/Z 355 (M+H)+ ; calculated for C19H22N4O3. 0.4 H2O: C, 63.1%; H, 6.36%; N, 15.5%; found: C, 63.1%; H, 6.4%; N, 15.7%.

Workup

  1. customa precipitate was collected
  2. washwashed with DMF and ethanol
  3. customdried

Sources & evidence

ORD record
ord-45290fee3adc4a0d9f2951dcce3f9500
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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