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

HRID 1292981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292981
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f8f675fcfec54029aa83c1745a9af4ae
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238696B2

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