反応 #8468

反応方程式

product

2-(4′-chloropropoxy-3′-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine hydrobromide

piperidine

→

title compound

2-(4′-piperidinopropoxy-3′-methoxyphenyl)-7-methylimidazo[1,2-a]pyridine

反応条件

後処理

1. 1
   その他partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
2. 2
   抽出The aqueous portion was extracted twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL)
3. 3
   洗浄washed with brine
4. 4
   その他evaporated
5. 5
   その他The residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol)

実験手順

The product of Step C (184 mg) and piperidine (1.5 mL) were heated at 100° C. for 4 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL). The organic portions were combined, washed with brine, and evaporated. The residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol) to give the title compound (150 mg). 1H-NMR (CD3OD) δ 8.17 (d, J=7.0 Hz, 1H), 7.93 (s, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.38 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 7.26 (s, 1H), 6.93 (d, J=8.0 Hz, 1H), 6.68 (dd, J=7.0 Hz, J=1.5 Hz, 1H), 4.00 (t, J=6.0 Hz, 2H), 3.91 (s, 3H), 2.56 (m, 3H), 2.48 (br. s, 3H), 2.38 (s, 3H), 1.98 (m, 2H), 1.60 (m, 4H), 1.47 (m, 2H)

出典