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

HRID 1157603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157603
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0681944e788d43da90867961e4cec6a6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807673B2

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