Triethylamine → 3-(1-Propyn-1-yl)-1-(2-thiophenylsulfonyl)piperazine
Reaction equation
[C:1]([CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1)#[C:2][CH3:3].FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.C(C1CNCCN1)#CC.C(N(CC)CC)C.[S:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[C:1]([CH:4]1[NH:5][CH2:6][CH2:7][N:8]([S:45]([C:41]2[S:40][CH:44]=[CH:43][CH:42]=2)(=[O:47])=[O:46])[CH2:9]1)#[C:2][CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The 2-(1-propyn-1-yl)piperazine bis(trifluoroacetate (110 mg, 0.312 mmol) was dissolved in CH2Cl2 in a 50 mL round-bottomed flask and was then cooled to 0° C. To this solution was added an excess of triethylamine (152 μL, 1.093 mmol) followed by thiophene-2-sulfonyl chloride (57.0 mg, 0.312 mmol, Sigma-Aldrich, St. Louis, Mo.). The mixture was warmed slowly to room temperature and stirred for 2 h. Afterwards, the mixture was concentrated and absorbed onto silica gel. The crude material was purified via column chromatography (about 40 g silica gel, 0% to 10% MeOH in CH2Cl2) to give 3-(1-propyn-1-yl)-1-(2-thiophenylsulfonyl)piperazine (42 mg) as a foamy solid.
Workup
- temperatureThe mixture was warmed slowly to room temperature
- concentrationAfterwards, the mixture was concentrated
- customabsorbed onto silica gel
- customThe crude material was purified via column chromatography (about 40 g silica gel, 0% to 10% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-68114e47dbb64e71a46f68c3ddfdc81d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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