反应详情

A mixture containing 2,2-diphenyl-5-methylaminopentanamide (0.36 g-see Preparation 3), 4-hydroxyphenethyl bromide (0.26 g), sodium bicarbonate (0.5 g) and acetonitrile (20 ml) was heated under reflux for 16 hours. The mixture was partitioned between dichloromethane (40 ml) and aqueous sodium bicarbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (2×30 ml). The combined dichloromethane extracts were concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give a foam which was further purified by column chromatography on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield 0.09 g.

1. temperaturewas heated
2. temperatureunder reflux for 16 hours
3. customThe mixture was partitioned between dichloromethane (40 ml) and aqueous sodium bicarbonate (30 ml)
4. customthe layers separated
5. extractionthe aqueous layer extracted with dichloromethane (2×30 ml)
6. concentrationThe combined dichloromethane extracts were concentrated in vacuo
7. customto give an oil which
8. customwas purified by column chromatography on silica eluting with dichloromethane
9. additioncontaining methanol (0% up to 10%)
10. concentrationconcentrated in vacuo
11. customto give a foam which
12. customwas further purified by column chromatography on alumina eluting with dichloromethane
13. additioncontaining methanol (0% up to 10%)
14. concentrationconcentrated in vacuo