8-Bromooct-1-ene → HCID 10473256、化合物

HRID 9794

反応式

HRID 9794 の反応式
[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

参加物

4

反応物 2

HCID 759078-Bromooct-1-eneHCID 89594Nicotine

生成物 1

HCID 10473256HCID 10473256、化合物収率 77%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-44caa68fa2d0420e80f2c7acc69a0271
出典データセット
uspto-grants-2006_08
特許番号
US07091357B2

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