Compound 90
5,6-dimethoxy-2-((1-phenylpiperidin-4-yl)methyl)-2,3-dihydro-1H-inden-1-one
From: Practical and regioselective amination of arenes using alkyl amines
View in PubChem | MDL Molfile | Chemdraw file
Compound data: NMR
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), desbenzyl donezepil (29 mg, 0.1 mmol) gave 90 (20 mg, 55%) as an oil. Rf 0.07 [petrol–EtOAc (8:2)]; FT-IR νmax (film)/cm–1 3010, 2924, 1695, 1476, 1456, 1312, 1261, 1033; 1H NMR (400 MHz, CDCl3) δ 7.39–7.30 (3H, m), 7.04 (2H, d, J = 8.2 Hz), 6.95 (1H, s), 6.92 (1H, t, J = 7.3 Hz), 4.04 (3H, s), 3.99 (3H, s), 3.83–3.70 (2H, m), 3.36 (1H, dd, J = 17.3, 8.0 Hz), 2.91–2.69 (4H, m), 2.12–2.00 (1H, m), 1.99–1.83 (3H, m), 1.64–1.41 (3H, m); 13C NMR (126 MHz, CDCl3) δ 207.8, 155.7, 151.8, 149.6, 148.9, 129.4, 129.2, 119.7, 116.8, 107.5, 104.5, 56.4, 56.3, 50.3, 45.4, 38.9, 34.5, 33.5, 33.0, 31.8; HRMS (ASAP POS): Found MH+ 366.2057, C23H28NO3 requires 366.2064.
