1-(4-Pyridyl)piperazine → Ethyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

HRID 266740

Reaction equation

HRID 266740 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(#N)C>[N:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH2:2][C:3]([C:5]3[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18408936Ethyl 2-[4-(2-bromoacetyl)phenoxy]acetate

Product 1

HCID 18918266Ethyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 4-bromoacetylphenoxyacetate (6.0 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed by filtration. The filtrate was evaporated in vacuo and the solid residue triturated with water, filtered, then washed with water and dried. Recrystallisation from a small volume of ethanol gave the title compound, 1.71 g, as a cream coloured solid: m.p. 113°-114° C.; (d6DMSO) δ 8.15 (2H, d), 7.98 (2H, d), 7.02 (2H, d), 6.80 (2H, d), 4.89 (2H, d), 4.17 (2H, q), 3.84 (2H, s), 3.32 (4H, t), 2.62 (4H, t), 1.22 (3H, t); m/e 384 (M+H)+ ; calculated for C21H25N3O4 : C, 65.8; H, 6.6; N, 11.0. found: C, 65.5; H, 6.6; N, 10.8%.

Workup

  1. customovernight at ambient temperature when the precipitated solid was removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe solid residue triturated with water
  4. filtrationfiltered
  5. washwashed with water
  6. customdried
  7. customRecrystallisation from a small volume of ethanol

Sources & evidence

ORD record
ord-2be04a7ca45447cfba0de30476c8ee08
Source dataset
uspto-grants-1997_07
Patent number
US05652242

Linked notes

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