反応 #4827

反応方程式

3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]-pyridine

dibutylaminopropyl chloride

potassium hydroxide

→

title compound

3-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

溶媒

methanol

反応条件

後処理

1. 1
   温度at reflux for 96 hours
2. 2
   濃縮The mixture was concentrated
3. 3
   その他chromatographed (silica gel, 2.5% methanol in diethyl ether)

実験手順

A mixture of 3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]-pyridine (2.3 g, 9.6 mmol), dibutylaminopropyl chloride (6.8 g, 33 mmol) and potassium hydroxide (1.3 g, 23 mmol) in methanol (60 ml) was stirred at reflux for 96 hours. The mixture was concentrated and the resulting oil was flash chromatographed (silica gel, 2.5% methanol in diethyl ether) to give 1.3 g (31% yield) of the free base of the title compound. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the free base in methanol, concentrated and recrystallized from acetone-ether to give the HCl salt of the title compound as an off-white solid, mp 105° C. to 107° C. lR(KBr): 3440, 2640, 1645, 1605 cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ9.66 (d, J=8 Hz, 1H), 8.74 (s, 1H), 8.00-7.61 (m, 4H), 7.20 (d, J=7.2 Hz, 2H), 4.29 (t, J=5 Hz, 2H), 3.41-3.15 (m, 6H), 2.75 (s, 3H), 2.31 (m, 2H), 1.80-1.42 (m, 8H), 1.02 (m, 6H).

出典