Nicotine → (s)-cis-1-Dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide salt

HRID 9793

反応式

HRID 9793 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]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(O)=O>[BrH:13].[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][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

4

反応物 2

HCID 89594NicotineHCID 10932932(Z)-1-Bromo-4-decene

生成物 1

HCID 69596039(s)-cis-1-Dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide salt収率 54%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of (S)-nicotine (0.35 g, 2.2 mmol) in AcOH (10 ml) was added cis-1-bromo-dec-4-ene (1.15 g, 5.25 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-cis-1-dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide hydrobromide salt (NDNB-4c) (0.54 g, 54%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 11.93 (1H, s), 10.75 (1H, s), 9.78 (1H, d, J=7.8 Hz), 8.69 (1H, d, J=6.0 Hz), 8.20 (1H, dd, J=7.8, 6.0 Hz), 5.88 (1H, m), 5.49 (1H, m), 5.30 (1H, m), 4.72 (2H, m), 4.01 (1H, m), 3.30 (1H, m), 2.97 (3H, d, J=5.1 Hz), 2.73 (1H, m), 2.10–2.60 (7H, m), 1.96 (2H, m), 1.70 (2H, m), 1.15–1.40 (6H, m), 0.86 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 147.41, 146.38, 144.98, 134.68, 132.93, 128.93, 126.06, 67.20, 62.37, 56.07, 38.71, 32.00, 31.64, 31.38, 29.34, 27.61, 23.94, 22.74, 21.91, 14.32; Anal. Calcd for C20H34Br2N2.0.5H2O: C, 50.97; H, 7.49; N, 5.94. Found: C, 50.90; H, 7.55; N, 5.94.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. customAcOH was evaporated
  4. customthe residue was recrystallized in ethyl acetate-CHCl3

出典と根拠

ORDレコード
ord-46186120e63646d3982a402cf138b971
出典データセット
uspto-grants-2006_08
特許番号
US07091357B2

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