Piperazine → HCID 58996633, compound
Reaction equation
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[CH2:7][CH2:6]1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>>[O:11]=[S:8]1(=[O:12])[CH2:9][CH2:10][CH:5]([O:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:6][CH2:7]1Participants
Procedure
Ortho-fluoro bromobenzene was reacted with tetrahydro-thiopyran-3-ol to give 4-(2-Bromo-phenoxy)-tetrahydro-thiopyran in a manner similar to preparation 24A. 4-(2-Bromo-phenoxy)-tetrahydro-thiopyran (1.94 g, 7.10 mmol) is placed in DCM (70 mL) and calcium carbonate (2.84 g, 28.41 mmol) was added. To this mixture cooled to 0° C. in an ice bath was added meta-chloro peroxy-benzoic acid (6.13 g, 17.75 mmol 50%) in portions while monitoring the temperature. The mixture was allowed to warm to r.t and stirred for about 15 minutes. The mixture was filtered over celite, and washed with sodium bisulfite solution (2×250 mL) and sodium bicarbonate (2×250 mL). The mixture was then concentrated to an oil. Chromatography (EtOAc/hexanes) provided 4-(2-Bromo-phenoxy)-tetrahydro-thiopyran 1,1-dioxide (2.2 g, quant.) as a yellow solid. 4-(2-Bromo-phenoxy)-tetrahydro-thiopyran 1,1-dioxide was coupled to piperazine using the Buchwald chemistry described in preparation 1A to afford the title compound. LRMS (ESI+): 311.1 (M+1)
Sources & evidence
- ORD record
- ord-7e1c36cdd52c4c27ac68b1b58fce0bfd
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291619B2
Reaction notes
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