Methyl iodide → 4-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(4-pentylphenylsulfonamido)piperidinium iodide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:4][CH2:3]1.[CH3:29][I:30]>>[I-:30].[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:5]1([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:4][CH2:3][N+:2]([CH3:29])([CH3:1])[CH2:7][CH2:6]1)[CH3:28]Participants
3
Procedure
Ethyl 2-(1-methyl-4-(4-pentylphenylsulfonamido)piperidin-4-yl)acetate (100 mg, 0.244 mmol) was treated with MeI as described in Example 2a to yield crude title compound (133 mg, 98%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, 2H, J=8.0 Hz), 7.33 (d, 2H, J=8.0 Hz), 6.05 (s, 1H), 3.98 (q, 2H, J=6.7), 3.79-3.70 (m, 2H), 3.65-3.60 (m, 5H), 3.40 (s, 3H), 2.69 (t, 2H, J=7.0 Hz), 2.54 (s, 2H), 2.49-2.43 (m, 4H), 1.67-1.61 (m, 2H), 1.38-1.32 (m, 4H), 1.17 (t, 3H, J=6.4 Hz), 0.91 (t, 3H, J=6.7 Hz); MS ESI 425.3 [M+H]+, calcd for [C22H36N2O4S+H]+ 425.60.
Sources & evidence
- ORD record
- ord-4e7cbfbccc824b5bb2c281cd05873906
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680282B2
Reaction notes
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