反应详情

A mixture of 6,7-dimethoxy-1-isochromanmethylamine (18.0 g), benzaldehyde (9.7 g) and dry benzene (400 ml) is heated under reflux (Dean-Stark) for 18 hr. The solvent is removed under reduced pressure and the residue (27.0 g) is dissolved in ethanol (400 ml). Sodium borohydride (17.0 g) is added portionwise to the stirred solution. When the addition is complete the mixture is stirred and heated under reflux for 1.5 hr. and then left at room temperature overnight. The mixture is concentrated, diluted with water and extracted with ether. The ether extracts are in turn extracted with 10% HCl and these extracts are made alkaline and re-extracted with ether. These extracts are washed with brine, dried and evaporated to give the title compound, λmax EtOH 285 nm (3750) and 281 nm (4000).

1. temperatureis heated
2. temperatureunder reflux (Dean-Stark) for 18 hr
3. customThe solvent is removed under reduced pressure
4. dissolutionthe residue (27.0 g) is dissolved in ethanol (400 ml)
5. additionSodium borohydride (17.0 g) is added portionwise to the stirred solution
6. additionWhen the addition
7. temperatureheated
8. temperatureunder reflux for 1.5 hr
9. concentrationThe mixture is concentrated
10. additiondiluted with water
11. extractionextracted with ether
12. extractionextracted with 10% HCl
13. extractionre-extracted with ether
14. washThese extracts are washed with brine
15. customdried
16. customevaporated