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

HRID 1291870Notes

Reaction equation

HRID 1291870 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) δ 8.58 (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 C22H26N4 O5. 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-4c254587f22145bd8fbd4df796ac556e
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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