反应详情

2-Chloromethyl quinoline (3.6 g) was refluxed with 3-(6-benzyloxy-1-hydroxyhexyl)phenol (4.2 g), powdered potassium carbonate (8 g) and potassium iodide (0.2 g) in dry acetone (150 ml) overnight (16 hrs.). The suspension was filtered, the filtrate was concentrated in vacuo and then taken up in ethyl acetate. This solution was washed with 5% NaOH solution, water and brine and then dried. All solvent was removed to obtain the crude product which was purified by chromatography (silica gel; 30% ethyl acetate in hexanes). The pure compound was dissolved in ether, and was precipitated as the hydrochloride salt with a dry ethereal solution of HCl. The pure salt was filtered, washed with cold water, and dried in vacuo to yield a tan powder (1.5 g), mp 86°-89° C.

1. filtrationThe suspension was filtered
2. concentrationthe filtrate was concentrated in vacuo
3. washThis solution was washed with 5% NaOH solution, water and brine
4. customdried
5. customAll solvent was removed
6. customto obtain the crude product which
7. customwas purified by chromatography (silica gel; 30% ethyl acetate in hexanes)
8. dissolutionThe pure compound was dissolved in ether
9. customwas precipitated as the hydrochloride salt with a dry ethereal solution of HCl
10. filtrationThe pure salt was filtered
11. washwashed with cold water
12. customdried in vacuo