1-(4-Pyridyl)piperazine → Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenylacetate

HRID 864772

Reaction equation

HRID 864772 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)=[O:4].[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(#N)C>[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:23][CH2:24][N:25]([CH2:2][C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)=[O:4])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 11128026Benzeneacetic acid, 4-(chloroacetyl)-, methyl ester

Product 1

HCID 18918371Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenylacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl 4-chloroacetylphenylacetate (260 mg) in acetonitrile (4 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (375 mg) in acetonitrile (10 ml) and the mixture stirred overnight. The supernatent was decanted from the solid formed, concentrated in vacuo and purified by flash chromatography on neutral alumina, eluting with dichloromethane then 0.25% v/v methanol/dichloromethane and finally 0.5% v/v methanol dichloromethane. Concentration of the fractions in vacuo gave the title compound, 96 mg, as a white crystalline solid: m.p. 127°-129° C.; NMR (d6DMSO) δ8.15(2H,d), 7.98(2H,d), 7.41(2H,d), 6.81(2H,d), 3.91(2H,s), 3.78(2H,s), 3.53(3H,s), 3.33(4H,t), 2.64(4H,t); m/e 354(M+H)+ ; calculated for C20H23N3O3 : C, 68.0; H, 6.6; N, 11.9. found: C, 68.2; H, 6.6; N, 11.9%.

Workup

  1. customThe supernatent was decanted from the solid
  2. customformed
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography on neutral alumina
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7433a554da72415e82736ea18a52eac7
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Linked notes

Loading…