1-(4-Pyridyl)piperazine → Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]-2,2-dimethylacetyl]phenoxyacetate

HRID 1290527

Reaction equation

HRID 1290527 reaction equation
[CH3:1][C:2](Br)([CH3:17])[C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(#N)C>[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:2]([CH3:17])([CH3:1])[C:3]([C:5]3[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918473Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

Product 1

HCID 18918600Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]-2,2-dimethylacetyl]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate (1.58 g) was added to a stirred solution of 1-(4-pyridyl)piperazine (1.63 g) in acetonitrile (40 ml). After 34 days, the solid formed was removed by filtration and the filtrate evaporated to give an oil. Purification by flash chromatography on silica, eluting with 0.5 to 4.0% v/v methanol/dichloromethane gave the title compound, 240 mg, as a white foam: NMR (d6DMSO) δ8.49(2H,d), 8.12(2H,d), 6.96(2H,d), 6.77(2H,d), 4.87(2H,s), 3.69(3H,s), 3.28(4H,t), 2.58(4H,t), 1.25(6H,s); m/e 398 (M+H)+ ; calculated for C22H27N3O4. 0.25H2O; C, 65.7; H, 6.8; N, 10.4. found: C, 65.3; H, 6.9; N, 10.4%.

Workup

  1. customthe solid formed
  2. customwas removed by filtration
  3. customthe filtrate evaporated
  4. customto give an oil
  5. customPurification by flash chromatography on silica
  6. washeluting with 0.5 to 4.0% v/v methanol/dichloromethane

Sources & evidence

ORD record
ord-6a3d701db8254e6192a68951ad2aa912
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Linked notes

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