Methyl vinyl sulfone → 1-(2-Methoxy-5-nitrophenyl)-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 1157603Notes

Reaction equation

HRID 1157603 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH:18]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH2:19]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:19][CH2:18][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 37831381-(2-methoxy-5-nitrophenyl)piperazine

Product 1

HCID 595114221-(2-Methoxy-5-nitrophenyl)-4-[2-(methylsulfonyl)ethyl]piperazineYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The compound was synthesized by heating a solution of 1-[2-(methyloxy)-5-nitrophenyl]piperazine (0.5 g, 2.11 mmol) and methyl vinyl sulfone (0.336 g, 3.16 mmol) in iPrOH (25 mL) to reflux overnight. Reaction was cooled to rt and dried directly onto silica gel. Purified by silica gel chromatography 0-20% MeOH/NH4OH in EtOAc to obtain 0.5 g (69% yield) of the desired compound as a solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 2.6 (m, 4H) 2.7 (t, J=6.8 Hz, 2H) 3.0 (m, 8H) 3.9 (s, 3H) 7.1 (d, J=9.0 Hz, 1H) 7.6 (d, J=2.7 Hz, 1H) 7.9 (dd, J=9.1, 2.8 Hz, 1H).

Workup

  1. customThe compound was synthesized
  2. temperatureto reflux overnight
  3. customReaction
  4. customdried directly onto silica gel
  5. customPurified by silica gel chromatography 0-20% MeOH/NH4OH in EtOAc

Sources & evidence

ORD record
ord-0681944e788d43da90867961e4cec6a6
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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