Diisopropylethylamine → (3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine
Reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:16][C@H:17]1[CH2:22][NH:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:16][C@@H:17]1[NH:18][CH2:19][CH2:20][N:21]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:15])([F:14])[F:1])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH2:22]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-[(trifluoromethyl)oxy]benzenesulfonyl chloride (3.25 g, 12.48 mmol), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (2.5 g, 12.48 mmol) and DIPEA (4.58 ml, 26.2 mmol) in DCM (200 ml) was stirred at room temperature overnight. The mixture was washed with saturated aqueous NaHCO3 then brine. The organics were concentrated under vacuum, then re-dissolved in dioxane (200 ml). A 4M solution of HCl in dioxane (20 ml) and water (0.5 ml) were added and the mixture stirred overnight. The mixture was concentrated under vacuum, applied to an SCX-2 cartridge (20 g) washing with MeOH and eluting with 0.5M NH3 in MeOH; concentration under vacuum gave the title compound as a white solid (2.56 g).
Workup
- washThe mixture was washed with saturated aqueous NaHCO3
- concentrationThe organics were concentrated under vacuum
- dissolutionre-dissolved in dioxane (200 ml)
- additionA 4M solution of HCl in dioxane (20 ml) and water (0.5 ml) were added
- concentrationThe mixture was concentrated under vacuum
- washwashing with MeOH
- washeluting with 0.5M NH3 in MeOH
- concentrationconcentration under vacuum
Sources & evidence
- ORD record
- ord-b0c31701627748aab601d0d2a563c89b
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536183B2
Reaction notes
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