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

HRID 2102771Notes

Reaction equation

[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

Participants

Conditions

Temperature: -10 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f4be9bfdbe4f4e008037b5e21b514c9a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576087B2

Reaction notes

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