反応 #4825

反応方程式

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

→

title compound

収率 197.7%

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

収率 197.7%

溶媒

dibutylamine

反応条件

後処理

1. 1
   温度at reflux for 8 hours
2. 2
   その他The excess dibutylamine was removed by distillation
3. 3
   その他chromatographed (silica gel, acetone)

実験手順

A mixture of 2-(4-chloropropoxybenzoyl)-8-methylimidazo-[1,2-a]pyridine (2,4 g, 6.0 mmol) in dibutylamine (30 ml) was stirred at reflux for 8 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, acetone) to give the free base of the title compound (2.5 g, 100% yield) as a thick oil. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the title compound in methanol, concentrated and recrystallized from methanol-acetone, mp 159° C. to 161° C. IR(KBr): 3420, 1650cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ8.89 (s, 1H), 8.72 (d, J=6.6 Hz, 1H), 8.15 (d, J=8.9 Hz, 2H), 7.89 (d, J=7.3 Hz, 1H), 7.48 (t, J=6.9 Hz, 1H), 7.21 (d, J= 8.9 Hz, 2H), 4.29 (t, J=7 Hz, 2H), 3.26 (m, 6H), 2.73 (s, 3H), 2.33 (m, 2H), 1.79-1.35 (m, 8H), 1.02 (m, 6H).

出典