Reacción #9895

Ecuación de reacción

(S)-nicotine

11-bromo-undec-1-ene

→

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

Rendimiento 67.0%

Disolventes

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturaat reflux for 3 days
3. 3
   OtroAcOH was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   LavadoThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
6. 6
   Otrodried
7. 7
   OtroEvaporation of the solvent

Procedimiento

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.

Fuente