Compound 38
2-(4-(piperidin-1-yl)benzyl)pyridine
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) but using 6.0 equiv. of HClO4, 2-benzylpyridine (32 µL, 0.2 mmol) gave a mixture of 38 and 38* as an oil (14 mg, 52%). 38:38* = 3.3:1. Rf 0.17 [petrol–EtOAc (4:1)]; FT-IR νmax (film)/cm–1 2933, 2850, 2788, 1611, 1589, 1513, 1451, 1432, 1382, 1335, 1130; 1H NMR (400 MHz, CDCl3) δ 8.53 (1H, dd, J = 5.2, 2.2 Hz), 7.55 (1H, td, J = 7.6, 1.9 Hz), 7.16–7.11 (2H, m), 7.11–7.05 (2H, m), 6.91–6.86 (2H, m), 4.07 (2H, s), 3.13–3.09 (4H, m), 1.73–1.65 (4H, m), 1.59–1.51 (2H, m); 13C NMR (100 MHz, CDCl3) δ 161.7, 150.8, 149.2, 136.5, 130.1, 129.7, 123.0, 121.0, 116.8, 50.9, 43.9, 25.9, 24.3; HRMS (APCI): Found MH+ 253.1700, C17H21N2 requires 253.1699.
