Reacción #8468

Ecuación de reacción

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
2. 2
   ExtracciónThe aqueous portion was extracted twice with additional ethyl acetate (10 mL) and once with dichloromethane (10 mL)
3. 3
   Lavadowashed with brine
4. 4
   Otroevaporated
5. 5
   OtroThe residue was purified via silica gel chromatography (dichloromethane/2M ammonia in methanol)

Procedimiento

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)

Fuente