Dichloromethane → 3-((6-Methoxy-2-pyridinyl)methyl)-1-(2-thiophenylsulfonyl)piperazine

HRID 1972665Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][CH:10]2[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[S:28](Cl)(=[O:30])=[O:29].C(Cl)Cl>C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][CH:10]2[NH:11][CH2:12][CH2:13][N:14]([S:28]([C:24]3[S:23][CH:27]=[CH:26][CH:25]=3)(=[O:30])=[O:29])[CH2:15]2)[CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100-mL round-bottomed flask were added 2-((6-methoxy-2-pyridinyl)methyl)piperazine (373 mg, 1.80 mmol), triethylamine (0.375 mL, 2.70 mmol), 2-thiophenesulfonyl chloride (0.328 mL, 1.80 mmol, Aldrich, St. Louis, Mo., and DCM (5 mL). The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was diluted with saturated NaHCO3 (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 10% MeOH/EtOAc to give 3-((6-methoxy-2-pyridinyl)methyl)-1-(2-thiophenylsulfonyl)piperazine (135 mg) as viscous oil.

Workup

extractionextracted with EtOAc (2×30 mL)
extractionThe organic extract
washwas washed with saturated NaCl (5 mL)
dry with materialdried over Na2SO4
filtrationThe solution was filtered
concentrationconcentrated in vacuo
customto give the crude material as light-yellow oil
customThe crude product was purified by silica gel chromatography
washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record: ord-9c5554b45769456389d4224c3896c285
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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