Nicotine → (S)-1-[2-(2-ethoxy-ethoxy)-ethyl]-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide

HRID 9825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 9825
[N:1]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21]>CC(O)=O>[Br-:13].[CH2:15]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][N+:1]1[CH:2]=[CH:3][CH:4]=[C:5]([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:6]=1)[CH3:14]

Komponenten

4

Edukt 2

HCID 89594NicotineHCID 70153241-Bromo-2-(2-ethoxyethoxy)ethane

Produkt 1

HCID 11725974(S)-1-[2-(2-ethoxy-ethoxy)-ethyl]-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-nicotine (0.67 g, 4.1 mmol) in AcOH (20 ml) was added 1-bromo-2-(2-ethoxy-ethoxy)-ethane (1.97 g, 10.0 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 0.56 g (38%) of (S)-1-[2-(2-ethoxy-ethoxy)-ethyl]-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NONB-3O6O) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.65 (1H, d, J=6.0 Hz), 9.26 (1H, s), 8.44 (1H, d, J=7.8 Hz), 7.99 (1H, dd, J=7.8, 6.0 Hz), 5.27 (2H, t, J=4.8 Hz), 4.06 (2H, t, J=4.8 Hz), 3.64 (2H, m), 3.41–3.60 (5H, m), 3.26 (1H, m), 2.43 (2H, m), 2.25 (3H, s), 1.91 (2H, m), 1.60 (1H, m), 1.16 (3H, t, J=6.9 Hz); 13C NMR (75 MHz, CDCl3) δ 145.87, 144.40×2, 144.02, 127.85, 70.83, 69.72, 69.57, 67.17, 66.77, 61.41, 56.91, 40.67, 36.02, 23.41, 15.47; Anal. Calcd for C16H27BrN2.0.5H2O: C, 52.18; H, 7.66; N, 7.61. Found: C, 52.22; H, 7.68; N, 7.50.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. customAcOH was evaporated
  4. dissolutionthe residue was dissolved in CHCl3
  5. washThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
  6. customdried
  7. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-830166ec73f84d72856962a7dc3cd600
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091357B2

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