((Chloromethyl)sulphonyl)benzene → 1-Methyl-4-{5-nitro-6-[(phenylsulfonyl)methyl]pyridin-2-yl}piperazine

HRID 854390

Reaktionsgleichung

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.Cl[CH2:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20].CC([O-])(C)C.[K+]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH2:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[N:9]=2)[CH2:4][CH2:3]1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A stirred solution of 1-methyl-4-(5-nitropyridin-2-yl)piperazine (1.10 g, 5.00 mmol) and chloromethylphenylsulfone (0.950 g, 5.00 mmol) in dry THF, under nitrogen, is cooled to −60° C., treated with 1.0 M KOtBu in THF (10.0 mL, 10.0 mmol), allowed to warm to −10° C. over a 1 h period, quenched with acetic acid, treated sequentially with water and saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from EtOAc to give the title compound as a yellow solid, 1.60 g (85% yield), mp: 170°-172° C., identified by mass spectral and NMR analyses.

Aufarbeitung

customquenched with acetic acid
additiontreated sequentially with water and saturated aqueous NaHCO3
extractionextracted with CH2Cl2
washThe combined extracts are washed sequentially with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resultant residue is crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-b2b1b7e7168c4801a901b747bde79773
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07259165B2

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