Diethyl Ether → 1-(5-Cyclohexyl-pentyl)-3-phenylquinolinium iodide
Reaction equation
[C:1]1([NH:7][C:8]2C=N[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:30]COCC>>[I-:18].[CH:24]1([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N+:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:30]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1Participants
Procedure
A solution of Phenyl-quinolin-3-yl-amine (100 mg, 0.45 mmol) toluene (2 ml) and 5-iodo-pentyl-benzene (373 mg, 1.36 mmol) in a sealed pressure tube was stirred at 110° C. for 24 hours. The reaction mixture was cooled to room temperature, diluted with Et2O (15 ml) and the precipitated compound was filtered and washed with Et2O (3×20 ml). The crude product was purified on a chromatographic column using methanol as an eluent to yield a pure product as an orange solid (75 mg, mp 140-141° C.). 1H NMR (CD3OD): δ 1.42-1.56 (m, 2H), 1.66-178 (m, 2H), 2.04-2.18 (m, 2H), 2.58-2.68 (t, 2H, J=7.2 Hz), 4.88-5.04 (t, 2H, J=7.8 Hz), 7.08-7.24 (m, 6H), 7.14 (dd, 2H, J=0.9, 7.5 Hz), 7.40-7.44 (t, 2H, J=8.4 Hz), 7.76-7.84 (t, 1H, J=7.5 Hz), 7.86-7.94 (m, 1H), 8.08 (d, 1H, J=8.4 Hz), 8.30 (d, 1H, J=9.0 Hz), 8.46 (d, 1H, J=2.4 Hz), 9.04 (d, 1H, J=2.7 Hz). Anal Calcd for: C26H27IN2.1H2O: C, 60.92; H, 5.70; N, 5.47. Found: C, 60.79; H, 5.33; N, 6.38.
Workup
- filtrationthe precipitated compound was filtered
- washwashed with Et2O (3×20 ml)
- customThe crude product was purified on a chromatographic column
Sources & evidence
- ORD record
- ord-5ac1433699534da58622a5193be68f38
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703798B2
Reaction notes
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