反应详情

温度

20 °C

A mixture of 3-piperidinomethyl phenol (0.876 kg; 4.582 moles), 1-butoxy-2-(3-bromopropylamino)-1-cyclobutene-3,4-dione [prepared in Example 10] (1 kg; 3.446 moles), finely powdered (pulverized) potassium carbonate (0.633 kg; 4.582 moles), tris[2-(2-methoxyethoxy)ethyl]amine (0.234 kg; 0.725 mole) in dichloromethane (17.23L) was stirred at 20° C. for 40 hours. The mixture was washed with 3% aqueous sodium hydroxide (2×3L) and then the organic phase was concentrated to dryness under reduced pressure to an oil. The concentrate was diluted with toluene (10L), washed with water (3×2.5L), then extracted with 3N hydrochloric acid (2×2.5L). The cooled aqueous acidic phase was basified with 30% sodium hydroxide then extracted with dichloromethane (2×2.5L). The organic phase was treated with charcoal, stirred for 15 minutes, dried (over magnesium sulfate), filtered through diatomaceous earth and the pad washed with dichloromethane (3×0.25L). The combined filtrate was concentrated to dryness under reduced pressure to give 1300 g (94% yield) of the title compound as a yellowish oil.

1. washThe mixture was washed with 3% aqueous sodium hydroxide (2×3L)
2. concentrationthe organic phase was concentrated to dryness under reduced pressure to an oil
3. additionThe concentrate was diluted with toluene (10L)
4. washwashed with water (3×2.5L)
5. extractionextracted with 3N hydrochloric acid (2×2.5L)
6. extractionthen extracted with dichloromethane (2×2.5L)
7. additionThe organic phase was treated with charcoal
8. stirringstirred for 15 minutes
9. dry with materialdried (over magnesium sulfate)
10. filtrationfiltered through diatomaceous earth
11. washthe pad washed with dichloromethane (3×0.25L)
12. concentrationThe combined filtrate was concentrated to dryness under reduced pressure