8-Bromooct-1-ene → HCID 10473256, compound

HRID 9794

Reaction equation

HRID 9794 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][CH2:19][CH:20]=[CH2:21]>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]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14])[CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 759078-Bromooct-1-eneHCID 89594Nicotine

Product 1

HCID 10473256HCID 10473256, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (S)-nicotine (0.12 g, 0.71 mmol) in AcOH (2 ml) was added 8-bromo-oct-1-ene (0.34 g, 1.8 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 0.19 g (77%) of (S)-3-(1-methyl-pyrrolidin-2-yl)-1-oct-7-enyl-pyridinium bromide (NONB-7e) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.70 (1H, d, J=6.0 Hz), 9.21 (1H, s), 8.41 (1H, d, J=8.1 Hz), 8.08 (1H, dd, J=8.1, 6.0 Hz), 5.72 (1H, m), 4.86–5.10 (4H, m), 3.50 (1H, t, J=8.4 Hz), 3.22 (1H, m), 2.41 (2H, m), 2.20 (3H, s), 1.80–2.10 (6H, m), 1.61 (1H, m), 1.20–1.44 (6H, m); 13C NMR (75 MHz, CDCl3) δ 146.12, 144.00, 143.28, 142.63, 138.22, 128.05, 114.20, 66.68, 61.67, 56.48, 40.29, 35.67, 33.30, 31.88, 28.33, 28.27, 25.76, 22.98; Anal. Calcd for C18H29BrN2.0.35HBr: C, 56.65; H, 7.75; N, 7.34. Found: C, 56.96; H, 7.98; N, 6.95.

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-44caa68fa2d0420e80f2c7acc69a0271
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Linked notes

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