Nicotine → (S)-1-(7-Methyl-oct-6-enyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide

HRID 9821Notes

Reaction equation

HRID 9821 reaction equation
[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][CH2:16][CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21]>CC(O)=O>[BrH:13].[Br-:13].[CH3:21][C:20]([CH3:22])=[CH:19][CH2:18][CH2:17][CH2:16][CH2:15][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

Participants

4

Reactant 2

HCID 89594NicotineHCID 219886748-Bromo-2-methyl-oct-2-ene

Product 1

HCID 69596141(S)-1-(7-Methyl-oct-6-enyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stired solution of (S)-nicotine (0.33 g, 2.0 mmol) in AcOH (10 ml) was added 8-bromo-2-methyl-oct-2-ene (1.05 g, 5.12 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to (S)-1-(7-methyl-oct-6-enyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide (NONB-6e7M) (0.58 g, 63%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 11.61 (1H, s), 10.38 (1H, s), 9.52 (1H, d, J=8.1 Hz), 9.17 (1H, d, J=6.0 Hz), 8.31 (1H, dd, J=8.1, 6.0 Hz), 5.75 (1H, m), 5.03(1H, m), 4.81 (2H, m), 4.00 (1H, m), 3.37 (1H, m), 2.98 (3H, s), 1.80–2.25 (4H, m), 1.64 (3H, s), 1.55 (3H, s), 1.39 (4H, m); 13C NMR (75 MHz, CDCl3) δ 147.49, 146.49, 144.86, 134.65, 132.20, 128.91, 123.74, 67.14, 62.95, 56.09, 38.69, 32.02, 31.67, 29.34, 27.87, 26.04, 21.91, 18.05; Anal. Calcd for C19H32Br2N2.0.7H2O: C, 49.52; H, 7.28; N, 6.08. Found: C, 49.44; H, 7.18; N, 6.07.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. customAcOH was evaporated
  4. customthe residue was recrystallized in ethyl acetate-CHCl3 to (S)-1-(7-methyl-oct-6-enyl)-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide (NONB-6e7M) (0.58 g, 63%) as hygroscopic white crystals

Sources & evidence

ORD record
ord-8f398a8f4e7347fcb95044dd74345579
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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