Methyl iodide → 4-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(5-phenethylfuran-2-carboxamido)-piperidinium iodide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([NH:8][C:9]([C:11]2[O:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4][CH2:3]1.[CH3:30][I:31]>>[I-:31].[CH2:28]([O:27][C:25](=[O:26])[CH2:24][C:5]1([NH:8][C:9]([C:11]2[O:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4][CH2:3][N+:2]([CH3:30])([CH3:1])[CH2:7][CH2:6]1)[CH3:29]Participants
3
Procedure
Ethyl 2-(1-methyl-4-(5-phenethylfuran-2-carboxamido)piperidin-4-yl)acetate (25 mg, 0.063 mmol) was treated with MeI (38 uL, 0.630 mmol) as described in Example 2a to yield crude title compound (32 mg, 94%) which was used without further purification. NMR (400 MHz, CD3OD) δ 7.29-7.16 (m, 5H), 7.07 (s, 1H), 6.20 (s, 1H), 4.10 (q, 2H, J=7.2 Hz), 3.56-3.46 (m, 4H), 3.23 (s, 3H), 3.21 (s, 3H), 3.03 (s, 4H), 3.01 (s, 2H), 2.91-2.83 (m, 2H), 2.29-2.19 (m, 2H), 1.17 (t, 3H, J=7.2 Hz); MS ESI 414.1 [M+H]+, calcd for [C24H32N2O4+H]+ 413.53.
Sources & evidence
- ORD record
- ord-53c842c875f24fbd9ef8ab227edc1dd1
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680282B2
Reaction notes
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