Compound 22
1-(4-(trimethylsilyl)phenyl)piperidine
From: Practical and regioselective amination of arenes using alkyl amines
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP1 outlined for compound 4 in CH3CN, trimethyl(phenyl)silane (15 mg, 0.1 mmol) gave 22 and 22* (12 mg, 51%) as an inseparable mixture, as an oil. p:m = 1:1. 1H NMR (500 MHz, CDCl3, isomers) δ 7.42–7.36 (1H, m), 7.25 (0.5H, dd, J = 8.2, 7.1 Hz), 7.11 (0.5H, dd, J = 2.6, 1.0 Hz), 6.99 (0.5H, dt, J = 7.1, 1.1 Hz), 6.96–6.88 (1.5H, m), 3.22–3.15 (2H, m), 3.18–3.12 (2H, m), 1.78–1.65 (4H, m), 1.62–1.56 (2H, m), 0.25 (4.5H, s), 0.23 (4.5H, s); 13C NMR (126 MHz, CDCl3, isomers) δ 152.6, 151.9, 141.1, 134.4, 128.8, 128.6, 124.5, 122.0, 117.3, 115.6, 51.1, 50.1, 26.2, 25.9, 24.5, 24.5, –0.8, –0.9.
