((Chloromethyl)sulphonyl)benzene → 1-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazine

HRID 227293

Reaction equation

HRID 227293 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26].O(C(C)(C)C)[K]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[C:18]([CH2:24][S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81625((Chloromethyl)sulphonyl)benzeneHCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineHCID 178418922HCID 178418922, compound

Product 1

HCID 442428861-Benzyl-4-{4-nitro-3-[(phenylsulfonyl)methyl]phenyl}piperazineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

A stirred solution of 1-benzyl-4-(4-nitrophenyl)piperazine (5.95 g, 20.0 mmol) and chloromethylphenylsulfone (3.82 g, 20.0 mmol) in dry THF under nitrogen at −60° C. is treated with 1.0M KO-t-Bu in THF (44.0 mL, 44.0 mmol), warmed to −20° C. over a 1 h period, quenched with acetic acid and treated sequentially with water, saturated aqueous NaHCO3 and ether. The phases are separated and the aqueous phase is extracted with ether. The combined ethers are washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent) to give the title compound as a yellow solid, 7.52 g (83% yield), mp 145-146° C., characterized by NMR and mass spectral analyses.

Workup

  1. customquenched with acetic acid
  2. additiontreated sequentially with water, saturated aqueous NaHCO3 and ether
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with ether
  5. washThe combined ethers are washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is chromatographed (silica gel, 1:1 and 1:0 ethyl acetate:hexanes as eluent)

Sources & evidence

ORD record
ord-a74a25ab7e974c9e9b47fde5425c2c4f
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Linked notes

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