Reaction equation
[N:1]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH3:21]>CC(O)=O>[BrH:13].[Br-:13].[CH3:9][N:8]1[CH2:10][CH2:11][CH2:12][C@H:7]1[C:5]1[CH:6]=[N+:1]([CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH3:21])[CH:2]=[CH:3][CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of (S)-nicotine (0.47 g, 2.9 mmol) in AcOH (8 ml) was added cis-1-bromo-oct-3-ene (1.34 g, 7.00 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-cis-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridinium bromide hydrobromide salt (NONB-3c) (0.62 g, 49%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 12.19 (1H, s), 10.71 (1H, s), 9.74 (1H, d, J=7.8 Hz), 8.74 (1H, d, J=5.7 Hz), 8.16 (1H, dd, J=7.8, 5.7 Hz), 5.79 (1H, m), 5.58 (1H, m), 5.40 (1H, m), 4.82 (2H, m), 4.01 (1H, m), 3.03 (1H, m), 2.94 (3H, d, J=4.2 Hz), 2.20–2.90 (5H, m), 1.87 (1H, m), 1.70 (2H, m), 1.00–1.25 (4H, m), 0.79 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 146.96, 146.29, 145.29, 136.33, 134.12, 128.37, 121.81, 67.09, 62.01, 55.92, 38.53, 31.94, 31.41, 29.34, 26.94, 22.18, 21.72, 14.04; Anal. Calcd for C18H30Br2N2.0.4H2O: C, 48.97; H, 7.03; N, 6.35. Found: C, 49.00; H, 7.36; N, 6.39.
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 3 days
- customAcOH was evaporated
- customthe residue was recrystallized in ethyl acetate-CHCl3
Sources & evidence
- ORD record
- ord-f119762236ac4a1795b51bc76e49884b
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091357B2
Linked notes
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