Dichloromethane → Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate
Reaction equation
CO[C:3]1[CH:8]=[C:7](C)[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.CCN([CH2:20][CH3:21])CC.Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].[CH2:36](Cl)Cl>>[C:6]1([S:10]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])(=[O:11])=[O:12])[C:5]2[C:4](=[CH:36][CH:20]=[CH:21][CH:14]=2)[CH:3]=[CH:8][CH:7]=1Participants
5
Procedure
The sulfonyl chloride 1 (9.76 g, 85.2 mmol) and Et3N (11.8 ml, 85.2 mmol) were dissolved in CH2Cl2 (100 ml), and a solution of diphenylmethanamine (2, 15.61 g, 85.2 mmol) in CH2Cl2 (40 ml) was added dropwise in the course of 10 min. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was washed with aqueous 0.5 M KHSO4 (2×200 ml) and sat. NaCl solution (100 ml), dried over Na2SO4 and concentrated to dryness. Recrystallization from CH2Cl2 at 0-5° C. gave 17.63 g (79%) of the sulfonamide 3.
Workup
- washThe reaction mixture was washed with aqueous 0.5 M KHSO4 (2×200 ml) and sat. NaCl solution (100 ml)
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness
- customRecrystallization from CH2Cl2 at 0-5° C.
Sources & evidence
- ORD record
- ord-cf7f4129a0f24a0b98daca5c89f6ae79
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318769B2
Reaction notes
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