1-(4-Pyridyl)piperazine → HCID 18918516, compound

HRID 1290474Notes

Reaction equation

HRID 1290474 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:7][CH:6]=1)=[O:4].[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1>C(#N)C>[N:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:31][CH2:32][N:33]([CH2:2][C:3]([C:5]3[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)(=[O:16])=[O:15])=[CH:7][CH:6]=3)=[O:4])[CH2:34][CH2:35]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 18918520HCID 18918520, compound

Product 1

HCID 18918516HCID 18918516, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of N-(2-[4-bromoacetylphenyl]ethyl)-4-methylphenylsulphonamide (485 mg) in acetonitrile (10 ml) was added to a stirred solution of l-(4-pyridyl)piperazine (400 mg) in acetonitrile (10 ml) and the mixture was 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 crystallisation occured. These crystals on filtration and washing with dichloromethane gave the title compound, 230 mg, as an off-white solid: m.p. 133°-135° C.; NMR (d6DMSO) δ 8.14(2H,bd), 7.90(2H,d), 7.65(2H,d), 7.59(1H,t), 7.35(2H,d), 7.29(2H,d), 6.81(2H,d), 3.37(2H,s), 3.33(4H,t), 2.98(2H,q), 2.76(2H,t), 2.63(4H,t), 2.38(3H,s); m/e 479(M+H)+ ; calculated for C26H30N4O3S: C, 65.2; H, 6.3; N, 11.7; found. C 65.0; H, 6.3; N, 11.4%.

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 crystallisation
  5. filtrationThese crystals on filtration
  6. washwashing with dichloromethane

Sources & evidence

ORD record
ord-2e5e4af9060f408e85dbb6ac8feec2a5
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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