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 (0.46 g, 2.8 mmol) in AcOH (10 ml) was added trans-1-bromo-oct-3-ene (1.37 g, 7.17 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)-trans-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridinium bromide hydrobromide salt (NONB-3t) (0.76 g, 62%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 11.55 (1H, s), 10.27 (1H, s), 9.46 (1H, d, J=7.5 Hz), 9.16 (1H, d, J=5.7 Hz), 8.22 (1H, dd, J=7.5, 5.7 Hz), 5.72 (1H, m), 5.41 (2H, m), 4.88 (2H, m), 3.98 (1H, m), 3.38 (1H, m), 2.94 (3H, s), 2.60–2.90 (3H, m), 2.43 (3H, m), 1.86 (2H, m), 1.00–1.25 (4H, m), 0.79 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 147.29, 146.41, 145.11, 137.58, 134.31, 128.44, 122.37, 67.18, 62.27, 56.04, 38.57, 34.49, 32.30, 32.00, 31.41, 22.32, 21.83, 14.12; Anal. Calcd for C18H30Br2N2.0.3H2O: C, 49.22; H, 6.93; N, 6.38. Found: C, 49.25; H, 7.03; N, 6.30.
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-d5252b372b2d4d16afed6358ce3bccce
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091357B2
Linked notes
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