Methyl vinyl sulfone → 1-[2-(Methanesulfonyl)ethyl]-4-(5-methoxy-2-methyl-4-nitrophenyl)piperazine

HRID 1014256Notes

Reaction equation

HRID 1014256 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH3:19][S:20]([CH:23]=[CH2:24])(=[O:22])=[O:21]>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:24][CH2:23][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 59441832HCID 59441832, compound

Product 1

HCID 534879841-[2-(Methanesulfonyl)ethyl]-4-(5-methoxy-2-methyl-4-nitrophenyl)piperazineYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperazine (0.300 g, 1.2 mmol) in 10 mL of dioxane was added, ethenyl methyl sulfone (0.32 g, 3 mmol). The mixture was heated to 120° C. 1 hour. The solvent was rotovaped down and the crude product was purified by flash chromatography, followed by a wash of the solids with 30% ether in hexanes to give 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine (0.257 g, 0.72 mmol, 60%). 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (s, 1 H), 6.54 (s, 1 H), 3.93 (s, 3 H), 3.18-3.30 (m, 2 H), 2.99-3.10 (m, 9 H), 2.71-2.82 (m, 4 H), 2.23 (s, 3 H).

Workup

  1. custom1 hour
  2. customthe crude product was purified by flash chromatography
  3. washa wash of the solids with 30% ether in hexanes

Sources & evidence

ORD record
ord-4fe8b1ddb44a4dcbb90d75658064339d
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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