Compound 77
N-(1-adamantan-1-yl)ethyl)aniline
From: Practical and regioselective amination of arenes using alkyl amines
View in PubChem | MDL Molfile | Chemdraw file
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, rimantadine hydrochloride (21.5mg, 0.1 mmol) gave 77 (7 mg, 25%) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.14 (2H, d, J = 7.8 Hz), 6.62 (1H, t, J = 7.2 Hz), 6.59 (2H, d, J = 8.6 Hz), 3.43 (1H, d, J = 9.9 Hz), 3.07 (1H, dq, J = 9.9, 6.6 Hz), 1.99 (3H, bs), 1.77–1.61 (9H, m), 1.59–1.45 (3H, m), .1.06 (3H, d, J = 7.7 Hz); 13C-NMR (75 MHz, CDCl3): δ 148.6, 129.1, 116.3, 112.5, 57.4, 38.7, 37.1, 36.5, 28.4, 14.4.
