Hexylamine → HCID 12045720, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure D, a mixture of 4-chloroanisole (1.23 mL, 10 mmol), hexylamine (1.83 mL, 14 mmol), NaOt-Bu (1.15 g, 12 mmol), 10 (4 mg, 0.05 mol %), 1 (2.5 mg, 0.05 mol %), and Bu2O (3 mL) was heated to 85° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 100 g; 0-50% EtOAc/hexanes) to provide the title compound as a yellow oil (1.828 g, 88%). 1H NMR (300 MHz, CDCl3) δ: 6.84 (d, J=9.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 3.78 (s, 3H), 3.40 (s, 1H), 3.09 (t, J=7.0 Hz, 2H), 1.64 (pentet, J=7.5 Hz, 2H), 1.42 (m, 6H), 0.97 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 152.2, 143.2, 115.1, 114.2, 56.0, 45.3, 32.0, 30.0, 27.2, 23.0, 14.4 ppm. IR (neat, cm−1): 3394, 2929, 2857, 2831, 1513, 1466, 1237, 1180, 1040, 819, 520.

Provenance & Evidence