Nicotine → (S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide

HRID 9817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 9817
[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][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(O)=O>[Br-:13].[CH2:14]([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)[CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Komponenten

4

Edukt 2

HCID 89594NicotineHCID 14534130HCID 14534130, Verbindung

Produkt 1

HCID 10407342(S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromideAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-nicotine (0.46 g, 2.8 mmol) in AcOH (15 ml) was added 1-bromo-dec-3-yne (1.50 g, 6.91 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 0.55 g (51%) of (S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NDNB-3y) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.77 (1H, d, J=5.7 Hz), 9.14 (1H, s), 8.43 (1H, d, J=8.1 Hz), 8.04 (1H, dd, J=8.1, 5.7 Hz), 5.16 (2H, m), 3.52 (1H, t, J=8.1 Hz), 3.27 (1H, m), 3.03 (2H, m), 2.47 (2H, m), 2.26 (3H, s), 1.85–2.10 (4H, m), 1.70 (1H, m), 1.15–1.45 (8H, m), 0.86 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 145.91, 144.24, 144.12, 143.57, 128.02, 86.16, 73.98, 67.24, 60.66, 56.87, 40.70, 36.05, 31.44, 28.86, 28.75, 23.36, 22.71, 22.45, 18.82, 14.27; Anal. Calcd for C20H31BrN2.0.7H2O: C, 61.28; H, 8.33; N, 7.15. Found: C, 61.14; H, 8.21; N, 7.14.

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-3fdcf2a8f87f46b7a88d01e0c4bc8690
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091357B2

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