Potassium Carbonate → N-(2-(1-benzylpiperidin-4-yl)ethyl)benzo[d]isoxazol-3-amine

Participants

Reaction Steps

The procedure described in Example 21 was followed with 3-chloro-1,2-benzisoxazole (0.682 g, 4.44 mmol), 4-aminoethyl-1-phenylmethyl piperidine (0.970 g, 4.44 mmol), and K2CO3 (0.614 g, 4.44 mmol) in DMSO (30 mL). After purification, the title compound (0.231 g, 15%) was obtained as a pale yellow oil. 1H-NMR (CDCl3) δ 7.45-7.54 (m, 2H), 7.24-7.40 (m, 6H), 7.19 (t, 1H, J=7.8 Hz), 4.40 (brt, 1H, J=5.5 Hz), 3.52 (s, 2H), 3.45 (dt, 2H, J=7.4 Hz, J=6.0 Hz), 2.91 (brd, 2H, J=11.8 Hz), 1.99 (brt, 2H, J=11.2 Hz), 1.62-1.73 (m, 4H), 1.37-1.52 (m, 3H). 13C-NMR (CDCl3) δ 162.7, 158.6, 137.8, 129.8, 129.4, 128.2, 127.1, 122.1, 119.8, 116.3, 110.0, 63.3, 53.6, 41.5, 36.1, 33.4, 32.0. EIMS: 335 (M+), 244, 199, 186, 172, 91 (base). HRMS calc'd. for C21H25N3O: 335.1998. Found: 335.1909.

Provenance & Evidence