Réaction #9900

Équation de réaction

(S)-nicotine

(6-bromo-hexyl)cyclobutane

→

(S)-1-(6-cyclobutyl-hexyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide salt

Rendement 61.0%

Solvants

AcOH

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureat reflux for 3 days
3. 3
   AutreAcOH was evaporated
4. 4
   Autrethe residue was recrystallized in ethyl acetate-CHCl3

Mode opératoire

To a stired solution of (S)-nicotine (0.18 g, 1.1 mmol) in AcOH (4 ml) was added (6-bromo-hexyl)cyclobutane (0.59 g, 2.7 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)-1-(6-cyclobutyl-hexyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide salt (NCyNB4) (0.31 g, 61%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 11.64 (1H, s), 10.42 (1H, s), 9.54 (1H, d, J=8.1 Hz), 9.06 (1H, d, J=6.0 Hz), 8.27 (1H, dd, J=8.1, 6.0 Hz), 5.74 (1H, m), 4.78 (2H, m), 3.98 (1H, m), 3.34 (1H, m), 2.96 (3H, d, J=5.1 Hz), 2.73 (1H, m), 2.44 (3H, m), 2.14 (3H, m), 1.96 (2H, m), 1.75 (2H, m), 1.51 (2H, m), 1.33 (6H, m), 1.16 (2H, m); 13C NMR (75 MHz, CDCl3) δ 147.61, 146.61, 144.67, 134.77, 128.91, 67.09, 63.07, 56.09, 38.71, 36.99, 36.17, 32.06, 31.76, 29.20, 28.60, 27.14, 26.53, 21.89, 18.72; Anal. Calcd for C20H34Br2N2.0.1H2O: C, 51.56; H, 7.44; N, 6.01. Found: C, 51.70; H, 7.45; N, 5.96.

Source