1-(4-Pyridyl)piperazine → HCID 18918480, compound

HRID 1291810Notes

Reaction equation

HRID 1291810 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:7][CH:6]=1)=[O:4].[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1>C(#N)C>[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:30][CH2:31][N:32]([CH2:2][C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][NH:12][S:13]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)(=[O:15])=[O:14])=[CH:7][CH:6]=3)=[O:4])[CH2:33][CH2:34]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918612HCID 18918612, compound

Product 1

HCID 18918480HCID 18918480, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of N-([4-bromoacetylphenyl]methyl)-4-methylphenylsulphonamide (470 mg) in acetonitrile (10 ml) was added to a stirred solution of 1-(4-pyridyl)piperazine (400 mg) in acetonitrile (10 ml) and the mixture stirred for 18 hours. The solvent was evaporated in vacuo and the residue purified by flash chromatography on silica, eluting with 10% v/v methanol/dichloromethane. On evaporation of the eluant fraction to a small volume crystallisation occurred. These crystals, on filtration and washing with dichloromethane gave the title compound, 130 mg, as a solid: m.p. 215°-219° C. dec.; NMR(d6DMSO) δ 8.14(3H,m), 7.91(2H,d), 7.69(2H,d), 7.38(4H,d), 6.82(2H,d), 4.03(2H,d), 3.89(2H,s), 3.32(4H,t), 2.62(4H,t), 2.39(3H,s); m/e 465(M+H)+ ; calculated for C25H28N4O3S: C, 64.6; N, 6.1; N, 12.1. found C, 64.7; H, 6.2; N, 12.0%.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified by flash chromatography on silica
  3. washeluting with 10% v/v methanol/dichloromethane
  4. customOn evaporation of the eluant fraction
  5. customto a small volume crystallisation
  6. filtrationThese crystals, on filtration
  7. washwashing with dichloromethane

Sources & evidence

ORD record
ord-431ef240799b462eb33519aa5feebbfd
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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