Nicotine → HCID 10383286, compound

HRID 9815Notes

Reaction equation

HRID 9815 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][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH3:21]>CC(O)=O>[Br-:13].[CH3:9][N:8]1[CH2:10][CH2:11][CH2:12][C@H:7]1[C:5]1[CH:6]=[N+:1]([CH2:14][CH2:15][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 89594NicotineHCID 124762061-Bromooct-3-yne

Product 1

HCID 10383286HCID 10383286, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (S)-nicotine (0.41 g, 2.5 mmol) in AcOH (10 ml) was added 1-bromo-oct-3-yne (1.16 g, 6.14 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 0.50 g (56%) of (S)-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-ynyl-pyridinium bromide (NONB-3y) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.74 (1H, d, J=5.1 Hz), 9.15 (1H, s), 8.43 (1H, d, J=7.8 Hz), 8.04 (1H, dd, J=7.8, 5.1 Hz), 5.13 (2H, m), 3.51 (1H, t, J=7.8 Hz), 3.23 (1H, m), 3.00 (2H, m), 2.42 (2H, m), 2.22 (3H, s), 2.01 (2H, m), 1.89 (2H, m), 1.64 (2H, m), 1.28 (4H, m), 0.82 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 145.97, 144.38, 144.10, 143.57, 128.00, 86.12, 74.07, 67.30, 60.72, 56.92, 40.74, 36.11, 30.94, 23.14, 22.50, 22.16, 18.54, 13.80; Anal. Calcd for C18H27BrN2.0.5H2O: C, 60.00; H, 7.83; N, 7.77. Found: C, 60.15; H, 7.92; N, 6.92.

Workup

  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

Sources & evidence

ORD record
ord-3a2e1c71b4a74113897194ff2892f23d
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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