Reacción #1355853

Ecuación de reacción

product

2-(4-chloropropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

piperidine

→

title compound

2-(4-Piperidinopropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature for 5 hours
2. 2
   Otropartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
3. 3
   ExtracciónThe aqueous portion was extracted with additional ethyl acetate (10 mL)
4. 4
   SecadoThe organic portions were dried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Procedimiento

The product of Step C (0.2 g) and piperidine (2.0 mL) were heated at reflux temperature for 5 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 with additional ethyl acetate (10 mL) and the organic portions combined. The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (0.21 g). This compound can also be named as 7-(methyl-2-[4-(3-piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine. Treatment with 2M HCl in ether afforded the dihydrochloride. 1H NMR (CD3OD) δ 8.67 (d, J=7.5 Hz, 1H), 8.41 (s, 1H), 7.84 (m, 2H), 7.71 (s, 1H), 7.36 (dd, J=6.9 Hz, J=1.4 Hz, 1H), 7.16 (m, 2H), 4.22 (t, J=5.8 Hz, 2H), 3.64 (d, J=12.5 Hz, 2H), 3.35 (m, 2H), 3.04 (m, 2H), 2.62 (s, 3H), 2.34 (m, 2H), 1.99 (m, 2H), 1.86 (m, 3H), 1.59 (m, 1H); 13C NMR (CD3OD) δ 161.0, 147.1, 141.1, 136.2, 128.5, 128.2, 120.3, 119.3, 115.8, 110.6, 109.9, 65.8, 55.0, 53.8, 24.5, 23.6, 22.1, 21.2, MS (M+H)=350.2 Analysis: Calc'd for C22H27N3O·2HCl·(2H2O)C, 57.64; H, 7.26; N, 9.17. Found: C, 57.68; H, 7.13; N, 9.16.

Fuente