Triethylamine → Methyl 5-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]benzofuran-2-carboxylate

HRID 864778Notes

Reaction equation

HRID 864778 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:21][C:22]([C:24]1[CH:25]=[CH:26][C:27]2[O:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][C:28]=2[CH:36]=1)=[O:23]>C(#N)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:21][C:22]([C:24]3[CH:25]=[CH:26][C:27]4[O:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][C:28]=4[CH:36]=3)=[O:23])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 18918450Methyl 5-(2-bromoacetyl)benzofuran-2-carboxylate

Product 1

HCID 18918243Methyl 5-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1-(4-pyridyl)piperazine (262 mg) and triethylamine (0.1 ml) in acetonitrile (10 ml) was added dropwise over 40 minutes a solution of methyl 5-(2-bromoacetyl)benzofuran-2-carboxylate in acetonitrile (5 ml). The resulting mixture was stirred for 2 hours, concentrated and purified by flash column chromatography on grade III alumina, eluting with methanol/dichloromethane (1:99 to 4:96 v/v) to give the title compound as a solid (138 mg); m.p. 173°-177° C.: NMR 2.66(4H,m), 3.8(4H,m), 3.91(3H,s), 4.00(2H,s), 6.82(2H,m), 7.8-8.5(6H,m); m/e 380 (M+H+); calculated for C21H21N3O4.0.5H2O: C, 64.9; H, 5.7; N, 10.8. Found: C, 65.2; H, 5.7; N, 10.9%. The starting ester was prepared as follows:

Workup

  1. concentrationconcentrated
  2. custompurified by flash column chromatography on grade III alumina
  3. washeluting with methanol/dichloromethane (1:99 to 4:96 v/v)

Sources & evidence

ORD record
ord-3a27a6d5b87146a68c72c3b6789a0e2a
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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