Chloroacetonitrile → HCID 59729268, compound

Participants

Reaction Steps

To a solution of 2-(piperidin-4-ylidene)-2-(pyridin-2-yl)acetonitrile (560 mg, 2.8 mmol) in THF (20 mL) was added NEt3 (5 mL, 38 mmol) and chloroacetonitrile (3 mL, 47 mmol) and the reaction was stirred 16 h. The resulting precipitates were filtered away and the filtrate concentrated to dryness. The residues was purified by silica gel chromatography (Biotage 40-short, 50% EtOAc/hexanes to 100% EtOAc/hexanes) to yield 52 (470 mg, 2.0 mmol, 71%) as a yellow solid. 1H NMR: (500 MHz, CDCl3) δ 8.64 (br d, J=4.9 Hz, 1H), 7.77 (ddd, J=7.9, 7.6, 1.9 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.27 (dd, J=7.6, 4.9 Hz, 1H), 3.58 (s, 2H), 2.94 (t, J=5.8 Hz, 2H), 2.91 (t, J=5.8 Hz, 2H), 2.83 (t, J=5.8 Hz, 2H), 2.67 (t, J=5.8 Hz, 2H); LC/MS: (ES+) m/z (M+H)+=239; HPLC Rt=0.99 min., column 0, conditions B.

Provenance & Evidence