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

HRID 1972658Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH:10]2[CH2:15][NH:14][CH2:13][CH2:12][NH:11]2)=[CH:7][CH:6]=[CH:5][N: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[C:8]([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:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100-mL round-bottomed flask was added 2-((2-methoxy-3-pyridinyl)methyl)piperazine (350 mg, 1.69 mmol), triethylamine (0.353 mL, 2.54 mmol), and 2-thiophenesulfonyl chloride (0.34 mL, 1.86 mmol, Aldrich, St. Louis, Mo.) in 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 a yellow glass. The crude product was purified by silica gel chromatography, eluting with 10% MeOH/EtOAc to give 3-((2-methoxy-3-pyridinyl)methyl)-1-(2-thiophenylsulfonyl)piperazine (202 mg) as a white solid.

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 a yellow glass
customThe crude product was purified by silica gel chromatography
washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record: ord-7648458c42374fd9a7491d058b85f988
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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