Diisopropylethylamine → (3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine
Reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.CCN(C(C)C)C(C)C.[F:24][C:25]([F:38])([F:37])[O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][C@@H:2]1[NH:3][CH2:4][CH2:5][N:6]([S:33]([C:30]2[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:37])[F:38])=[CH:32][CH:31]=2)(=[O:35])=[O:34])[CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,1-dimethylethyl(2S)-2-methyl-1-piperazinecarboxylate (2.50 g, 12.5 mmol), DIPEA (4.58 ml, 26.2 mmol) and 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (3.25 g, 12.5 mmol) in DCM (200 ml) was stirred at room temperature overnight. The mixture was washed with saturated aqueous NaHCO3, then brine and concentrated under vacuum. The residue was redissolved in 1,4-dioxane (200 ml), then 4M HCl in dioxane (20 ml) and water (0.5 ml) were added and the mixture stirred overnight. The mixture was concentrated under vacuum and applied to an SCX-2 cartridge (20 g) washing with MeOH. The product was eluted with 0.5M NH3 in MeOH; concentration left the title compound as a white solid (2.56 g).
Workup
- washThe mixture was washed with saturated aqueous NaHCO3
- concentrationbrine and concentrated under vacuum
- dissolutionThe residue was redissolved in 1,4-dioxane (200 ml)
- addition4M HCl in dioxane (20 ml) and water (0.5 ml) were added
- concentrationThe mixture was concentrated under vacuum
- washwashing with MeOH
- washThe product was eluted with 0.5M NH3 in MeOH
- concentrationconcentration
- waitleft the title compound as a white solid (2.56 g)
Sources & evidence
- ORD record
- ord-e59a0ab2afb54dbb9fa1d66eaa215d4b
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093249B2
Reaction notes
Loading…