반응 #9885

반응 방정식

(S)-nicotine

trans-1-bromo-dec-4-ene

→

(S)-trans-1-dec-4-enyl-3-(1-methyl-pyrrolidin -2-yl)-1-pyridinium bromide

수율 74.1%

용매

AcOH

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 3 days
3. 3
   기타AcOH was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   세척The mixture was washed with saturated aqueous NaHCO3, water and brine successively
6. 6
   기타dried
7. 7
   기타Evaporation of the solvent

실험 절차

To a stirred solution of (S)-nicotine (0.47 g, 2.9 mmol) in AcOH (15 ml) was added trans-1-bromo-dec-4-ene (1.55 g, 7.08 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 0.82 g (74%) of (S)-trans-1-dec-4-enyl-3-(1-methyl-pyrrolidin -2-yl)-1-pyridinium bromide (NDNB-4t) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.71 (1H, d, J=5.7 Hz), 9.07 (1H, s), 8.40 (1H, d, J=8.1 Hz), 8.08 (1H, dd, J=8.1, 6.0 Hz), 5.42 (2H, m), 5.00 (2H, t, J=6.9 Hz), 3.54 (1H, t, J=8.4 Hz), 3.25 (1H, m), 2.44 (2H, m), 2.25 (3H, s), 1.65–2.20 (8H, m), 1.66 (1H, m), 1.15–1.40 (6H, m), 0.87 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 146.50, 144.36, 143.79, 143.13, 128.52, 127.15, 67.05, 61.49, 56.86, 40.70, 36.07, 32.67, 31.76, 31.56, 29.27, 29.07, 23.39, 22.70, 14.27; Anal. Calcd for C20H33BrN2.0.3H2O: C, 62.10; H, 8.76; N, 7.24. Found: C, 62.03; H, 8.88; N, 7.12.

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