1-(4-Pyridyl)piperazine → HCID 18924123, compound

HRID 743827Notes

Reaction equation

HRID 743827 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1>C(#N)C>[N:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:28][CH2:29][N:30]([CH2:2][C:3]([C:5]3[CH:20]=[CH:19][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:31][CH2:32]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918385HCID 18918385, compound

Product 1

HCID 18924123HCID 18924123, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl N-[4-(bromoacetyl)phenoxyacetyl]glycinate (0.85 g) in acetonitrile (10 ml) was added to a stirred solution of 1-(4-pyridyl)piperazine (0.81 g) in acetonitrile (30 ml). After stirring overnight the solvent was removed in vacuo and the residue partitioned between water/ethyl acetate. The organic phase was washed with water, then dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica, eluting with 0 to 7.5% v/v methanol/dichloromethane. Evaporation of the fractions gave the title compound, 130 mg, as a foam: NMR (d6DMSO) δ8.58 (1H, t), 8.16 (2H, d), 8.01 (2H, d), 7.08 (2H, d), 6.83 (2H, d), 5.75 (1H, s), 4.68 (2H, s), 3.92 (2H, d), 3.84 (2H, s), 3.65 (3H, s), 3.34 (4H, t+H2O), 2.65 (4H, t); m/e 427 (M+H)+ ; calculated for C22H26N4O5. 0.5CH2Cl2 : C, 57.6; H, 5.8; N, 11.9. found: C, 57.8; H, 5.7; N, 12.0%.

Workup

  1. customwas removed in vacuo
  2. customthe residue partitioned between water/ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica
  7. washeluting with 0 to 7.5% v/v methanol/dichloromethane
  8. customEvaporation of the fractions

Sources & evidence

ORD record
ord-59e7e8b000b64209b33af9e33d78ef43
Source dataset
uspto-grants-1996_09
Patent number
US05556977

Reaction notes

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