4-Methylpyridine → HCID 66588673, compound

Participants

Reaction Steps

4-Methylpyridine (307 mg, 3.3 mmol), (3-bromopropyl)triethylammonium bromide (1.0 g, 3.3 mmol), and 4 mL DMF were stirred at 100° C. in a pressure vessel for 41 h. Precipitates formed during the reaction. After cooling down, the precipitates were filtered out and washed with CH2Cl2 to give 1-(3-triethylammoniopropyl)-4-methylpyridinium dibromide as a light pink solid (750 mg, 57%), which was used in the next aldol condensation without further purification. 1H NMR (400 MHz, CD3OD): δ 1.34 (t, J=7.0 Hz, 9 H), 2.50 (m, 2 H), 2.70 (s, 3 H), 3.35-3.47 (m, 8 H), 4.73 (t, J=7.8 Hz, 2 H), 7.99 (d, J=6.4 Hz, 2 H), 8.98 (d, J=6.4 Hz, 2 H); 13C NMR (100 MHz, CD3OD): δ 8.0, 22.1, 25.2, 54.4, 54.5, 58.3, 130.1, 145.2, 161.9; HRMS (FAB+): m/z=315.1428 [M-Br]+ (calcd for C15H28BrN2: 315.1430).

Provenance & Evidence