Triethylamine → 3,3-dimethyl-4-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-2-piperazinone
Reaction equation
[CH3:1][C:2]1([CH3:16])[N:7]([CH2:8][C@H:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH2:6][CH2:5][NH:4][C:3]1=[O:15].C(N(CC)CC)C.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:1][C:2]1([CH3:16])[N:7]([CH2:8][C@H:9]2[CH2:14][N:13]([S:29]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)(=[O:31])=[O:30])[CH2:12][CH2:11][NH:10]2)[CH2:6][CH2:5][NH:4][C:3]1=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 20-mL vial was charged with 3,3-dimethyl-4-((2R)-2-piperazinylmethyl)-2-piperazinone (0.104 g, 0.461 mmol), triethylamine (0.200 mL, 1.44 mmol), and CH2Cl2 (3 mL). To this mixture thiophene-2-sulfonyl chloride (0.0951 g, 0.521 mmol, Sigma-Aldrich, St. Louis, Mo.) in CH2Cl2 (1 mL) was added drop wise at room temperature. The clear solution was stirred at room temperature for 30 min and then the mixture was concentrated and dissolved in CH2Cl2 (20 mL). The organic phase was washed with water (2×20 mL) and saturated aqueous NaCl (20 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3,3-dimethyl-4-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-2-piperazinone (0.166 g) as an off-white foam.
Workup
- concentrationthe mixture was concentrated
- dissolutiondissolved in CH2Cl2 (20 mL)
- washThe organic phase was washed with water (2×20 mL) and saturated aqueous NaCl (20 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f3992ff5eb6a413289bdf370fb974a9c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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