Реакция #9895

Уравнение реакции

(S)-nicotine

11-bromo-undec-1-ene

→

(S)-3-(1-methyl-pyrrolidin-2-yl)-1-undec-10-enyl-pyridinium bromide

Выход 67.0%

Растворители

AcOH

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураat reflux for 3 days
3. 3
   ДругоеAcOH was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   ПромывкаThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
6. 6
   Другоеdried
7. 7
   ДругоеEvaporation of the solvent

Методика

To a stirred solution of (S)-nicotine (0.14 g, 0.86 mmol) in AcOH (4 ml) was added 11-bromo-undec-1-ene (0.50 g, 2.1 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried. Evaporation of the solvent followed by titration with ether afforded 0.22 g (67%) of (S)-3-(1-methyl-pyrrolidin-2-yl)-1-undec-10-enyl-pyridinium bromide (NUNB-10e) as a brown oil. 1H NMR (300 Mz, CDCl3) δ 9.61 (1H, d, J=5.7 Hz), 9.22 (1H, s), 8.40 (1H, d, J=8.1 Hz), 8.08 (1H, dd, J=8.1, 6.0 Hz), 5.77 (1H, m), 4.85–5.10 (4H, m), 3.54 (1H, t, J=8.1 Hz), 3.24 (1H, m), 2.43 (2H, m), 2.23 (3H, s), 1.80–2.15 (6H, m), 1.63 (1H, m), 1.10–1.44 (12H, m); 13C NMR (75 MHz, CDCl3) δ 146.43, 144.21, 143.65, 143.09, 139.05, 128.44, 114.16, 66.97, 62.02, 56.82, 40.62, 35.99, 33.88, 32.24, 29.44×2, 29.18×2, 28.98, 29.26, 23.33.

Источник