반응 #1355853

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product

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

piperidine

→

title compound

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

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후처리

1. 1
   온도at reflux temperature for 5 hours
2. 2
   기타partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
3. 3
   추출The aqueous portion was extracted with additional ethyl acetate (10 mL)
4. 4
   건조The organic portions were dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue was purified via silica gel chromatography (dichloromethane/methanol)

실험 절차

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.

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