1-(5-Chloro-2-nitrophenyl)-4-methylpiperazine → 1-{5-Chloro-2-nitro-3-{[(4-fluorophenyl)sulfonyl]methyl}phenyl}-4-methylpiperazine

HRID 227301Notes

Reaction equation

HRID 227301 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1.Cl[CH2:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].CC([O-])(C)C.[K+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 28296181-(5-Chloro-2-nitrophenyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxideHCID 589047911-Chloromethanesulfonyl-4-fluoro-benzene

Product 1

HCID 442429661-{5-Chloro-2-nitro-3-{[(4-fluorophenyl)sulfonyl]methyl}phenyl}-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture of 1-(5-chloro-2-nitrophenyl)-4-methylpiperazine (1.0 mmol) and chloromethyl-(4-fluorophenyl)sulfone (1.0 mmol) in THF is treated with 2.2 mL of a 1M KOt-Bu (2.2 mmol) solution in THF at −78° C., warmed to room temperature over a 2 h period, quenched with acetic acid and concentrated in vacuo. The resultant residue is partitioned between EtOAc and aqueous Na2CO3. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase is combined with the extracts, dried over Na2SO4 and concentrated to dryness in vacuo to afford the title product.

Workup

  1. customquenched with acetic acid
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is partitioned between EtOAc and aqueous Na2CO3
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-3eadec08c29a4541ab6365f82af9c31a
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Reaction notes

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