Compound 44
5-methoxy-8-(piperidin-1-yl)isoquinoline
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP1 outlined for compound 4, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, 5-methoxyisoquinoline (16 mg, 0.1 mmol) gave 44 (24 mg, 99%) as an oil. Rf 0.28 [petrol–Et2O–Et3N (90:10:1)]; FT-IR νmax (film)/cm–1 2976, 2878, 1471, 1283, 1227; 1H NMR (CDCl3, 500 MHz) δ 9.56 (1H, s), 8.52 (1H, d, J = 5.8 Hz), 7.96 (1H, d, J = 5.8 Hz), 7.03 (1H, d, J = 8.2 Hz), 6.89 (1H, d, J = 8.2 Hz), 3.96 (3H, s), 3.02 (4H, br s), 1.83 (4H, br p, J = 5.7 Hz), 1.78–1.54 (2H, m); 13C NMR (CDCl3, 126 MHz) δ 150.2, 148.9, 145.0, 142.7, 129.5, 124.5, 115.3, 115.0, 107.6, 55.67, 55.2, 26.6, 24.4; HRMS (APCI): Found MH+ 244.1423, C15H19N2O requires 243.1419.
