반응 #4381

반응 방정식

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

dimethylamine

dimethylamine hydrochloride

sodium cyanoborohydride

hydrogen chloride

→

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

용매

methanol

methanol

methanol

반응 조건

후처리

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
   기타The solvent was evaporated in vacuo
5. 5
   기타the residue partitioned between methylene chloride and water
6. 6
   기타the methylene chloride layer separated
7. 7
   세척washed with Na2S2O5 solution
8. 8
   건조The organic phase was dried over anhydrous potassium carbonate
9. 9
   기타evaporated in vacuo
10. 10
    기타to yield a yellow oil
11. 11
    기타The solvent was removed in vacuo
12. 12
    workup.DISSOLUTIONthe residue dissolved in 45 ml of refluxing ethyl acetate
13. 13
    기타Some slight turbidity was removed by filtration
14. 14
    여과through filter aid
15. 15
    workup.ADDITIONdiluted with 20 ml of diethyl ether
16. 16
    온도The solution was cooled overnight in a refrigerator
17. 17
    기타the resulting solid, 3.34 g, removed by filtration
18. 18
    기타The filtrate was evaporated in vacuo
19. 19
    기타the residue triturated with ether
20. 20
    기타to yield a second crop of off-white solid, 1.66 g
21. 21
    기타One recrystallization from ethyl acetate yielded pure 2-iodo-5-methoxy-N,N-dimethylalphapentylbenzenepropanamine hydrochloride, mp 100°-103° C.

실험 절차

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.

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