反应 #4381

反应方程式

1-(2-iodo-5-methoxyphenyl)heptan-2-one

dimethylamine

dimethylamine hydrochloride

sodium cyanoborohydride

hydrogen chloride

→

2-Iodo-5-methoxy-N,N-dimethylalphapentylbenzenepropanamine hydrochloride

溶剂

methanol

methanol

methanol

反应条件

后处理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued an additional two hours
3. 3
   workup.ADDITIONthe reaction mixture acidified to pH 1 by addition of concentrated hyirochloric acid
4. 4
   其他The solvent was evaporated in vacuo
5. 5
   其他the residue partitioned between methylene chloride and water
6. 6
   其他the methylene chloride layer separated
7. 7
   洗涤washed with Na2S2O5 solution
8. 8
   干燥The organic phase was dried over anhydrous potassium carbonate
9. 9
   其他evaporated in vacuo
10. 10
    其他to yield a yellow oil
11. 11
    其他The solvent was removed in vacuo
12. 12
    workup.DISSOLUTIONthe residue dissolved in 45 ml of refluxing ethyl acetate
13. 13
    其他Some slight turbidity was removed by filtration
14. 14
    过滤through filter aid
15. 15
    workup.ADDITIONdiluted with 20 ml of diethyl ether
16. 16
    温度The solution was cooled overnight in a refrigerator
17. 17
    其他the resulting solid, 3.34 g, removed by filtration
18. 18
    其他The filtrate was evaporated in vacuo
19. 19
    其他the residue triturated with ether
20. 20
    其他to yield a second crop of off-white solid, 1.66 g
21. 21
    其他One recrystallization from ethyl acetate yielded pure 2-iodo-5-methoxy-N,N-dimethylalphapentylbenzenepropanamine hydrochloride, mp 100°-103° C.

实验过程

A mixture of 13.0 g (0.036 mole) of 1-(2-iodo-5-methoxyphenyl)heptan-2-one, 46.6 ml (0.18 mole) of a solution of 3.86 M dimethylamine in methanol, 8.24 g (0.101 mole) of dimethylamine hydrochloride, 100 ml of methanol and 1.82 g (0.029 mole) of sodium cyanoborohydride was stirred overnight under an atmosphere of nitrogen. Stirring was continued an additional two hours and the reaction mixture acidified to pH 1 by addition of concentrated hyirochloric acid. The solvent was evaporated in vacuo, the residue partitioned between methylene chloride and water, and the methylene chloride layer separated, washed with Na2S2O5 solution followed by a washing with 3 M sodium hydroxide solution. The organic phase was dried over anhydrous potassium carbonate and evaporated in vacuo to yield a yellow oil. The oil was dissolved in methanol and the solution treated with ethereal hydrogen chloride to pH 5. The solvent was removed in vacuo and the residue dissolved in 45 ml of refluxing ethyl acetate. Some slight turbidity was removed by filtration through filter aid. The filtrate was cooled to room temperature and diluted with 20 ml of diethyl ether. The solution was cooled overnight in a refrigerator and the resulting solid, 3.34 g, removed by filtration. The filtrate was evaporated in vacuo, the residue triturated with ether and seeded to yield a second crop of off-white solid, 1.66 g. One recrystallization from ethyl acetate yielded pure 2-iodo-5-methoxy-N,N-dimethylalphapentylbenzenepropanamine hydrochloride, mp 100°-103° C.

来源