反应详情

A suspension of 7-(trifluoromethyl)-1,3,4,5-tetrahydro-3-hydroxy-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (1.0 g, 2.85 mmol; see Example 28E) in 20 ml of dichloromethane was treated with 3.6 ml of water followed by the addition of barium hydroxide octahydrate (1.89 g, 5.99 mmol) and benzyl trimethylammonium chloride (0.12 g, 0.63 mmol). A solution of 2-dimethylaminoethyl bromide, hydrobromide in 2 ml of water was added portionwise with a pipette. Vigorous stirring under argon was carried out for 72 hours. An additional 0.33 g of 2-dimethylaminoethyl bromide, hydrobromide was added and stirring was continued overnight. The reaction mixture was filtered. The dichloromethane layer was washed twice with water. Hydrochloric acid (1M) was added, the dichloromethane was removed in vacuo, the aqueous layer was washed three times with ethyl acetate, made basic with 1M sodium hydroxide solution, and washed three times with ethyl acetate. The ethyl acetate layers were dried over sodium sulfate and evaporated in vacuo to yield 0.52 g of a white solid. Evaporation in vacuo of the ethyl acetate layers from the 1M hydrochloric acid washes yielded 0.52 g of a tan solid which was dissolved in chloroform, treated with saturated hydrogen chloride-ether solution and triturated with ether.

1. stirringstirring
2. waitwas continued overnight
3. filtrationThe reaction mixture was filtered
4. washThe dichloromethane layer was washed twice with water
5. additionHydrochloric acid (1M) was added
6. customthe dichloromethane was removed in vacuo
7. washthe aqueous layer was washed three times with ethyl acetate
8. washwashed three times with ethyl acetate
9. dry with materialThe ethyl acetate layers were dried over sodium sulfate
10. customevaporated in vacuo