Dimethylformamide → HCID 66588703, compound

Participants

Reaction Steps

4-Methylpyridine (307 mg, 3.3 mmol), (3-bromopropyl)tripropylammonium bromide (1.0 g, 2.9 mmol), and 4 mL DMF were stirred at 100° C. in a pressure vessel for 14 h. After cooling down, the reaction mixture was added dropwise to a vigorously stirred diethyl ether (100 mL). The oily precipitates formed was collected and further purified by column chromatography (SiO2, gradient from 1:4 to 1:1 MeOH/CH2Cl2) to furnish 1-(3-tripropylammoniopropyl)-4-methylpyridinium dibromide as a colorless solid (484 mg, 38%). 1H NMR (400 MHz, CD3OD): δ 1.03 (t, J=7.0 Hz, 9 H), 1.77 (m, 6 H), 2.51 (m, 2 H), 2.70 (s, 3 H), 3.28 (m, 6 H), 3.49 (m, 2 H), 4.72 (t, J=7.8 Hz, 2 H), 7.99 (d, J=6.4 Hz, 2 H), 8.99 (d, J=6.4 Hz, 2 H); HRMS (FAB+): m/z=357.1906 [M-Br]+ (calcd for C18H34BrN2: 357.1900).

Provenance & Evidence