Piperazine → HCID 58996657, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:10])=[O:9].[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[CH3:13][CH:12]([CH3:14])[CH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:10])=[O:9]Participants
Procedure
To a solution of 1-bromo-2-isobutylsulfanyl-benzene (8.0 g, 32.6 mmol, 1.0 eq) in DCM (100 mL) at 0° C. was added CaCO3 (13.05 g, 130.4 mmol, 4.0 eq.) and MCPBA (28.1 g, 81.5 mmol, 2.5 eq.). The mixture was stirred for about 30 minutes and filtered through a pad of celite. The solution was washed with sodium bisulfite (2×) and 5N NaOH (2×). The organic layer was dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (250 g SiO2, linear gradient, 40 mL/min, 10%-40% EtOAC/hexane for about 33 minutes) afforded 1-bromo-2-(2-methyl-propane-1-sulfonyl)-benzene (7.4 g, 26.6 mmol, 82%). GCMS (EI): 276.0. 1-bromo-2-(2-methyl-propane-1-sulfonyl)-benzene was coupled to piperazine in a manner similar to Preparation 1A. LRMS (ESI+): 283.06 (M+1)
Sources & evidence
- ORD record
- ord-b407dbd9512e48d2b24cad23544ec041
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291619B2
Reaction notes
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