Reaktion #9892

Reaktionsgleichung

(S)-nicotine

10-bromo-dec-1-ene

→

(S)-1-dec-9-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide

Ausbeute 61.0%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux for 3 days
3. 3
   SonstigeAcOH was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   WaschenThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
6. 6
   Sonstigedried
7. 7
   SonstigeEvaporation of the solvent

Vorschrift

To a stirred solution of (S)-nicotine (0.52 g, 3.2 mmol) in AcOH (10 ml) was added 10-bromo-dec-1-ene (1.66 g, 7.58 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 0.74 g (61%) of (S)-1-dec-9-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NDNB-9e) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.65 (1H, d, J=5.1 Hz), 9.14 (1H, s), 8.41(1H, d, J=8.1 Hz), 8.09 (1H, dd, J=8.1, 5.1 Hz), 5.75 (1H, m), 4.88–5.10 (4H, m), 3.54 (1H, t, J=8.1 Hz), 3.23 (1H, m), 2.45 (2H, m), 2.22 (3H, s), 1.70–2.10 (6H, m), 1.61 (1H, m), 1.10–1.40 (10H, m); 13C NMR (75 MHz, CDCl3) δ 146.46, 144.39, 143.74, 142.97, 139.07, 128.50, 114.33, 67.17, 62.25, 56.92, 40.74, 36.11, 33.93, 32.35, 29.42, 29.24, 29.15, 29.03, 26.35, 23.41.

Quelle