반응 #63321

반응 방정식

3-(1-piperidinylmethyl)phenol

sodium hydride

N-(4-Bromobutyl)phthalimide

→

title compound

수율 34.4%

4-[3-(1-Piperidinylmethyl)phenoxy]butanamine

수율 34.4%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at 25° during 20 h
2. 2
   workup.WAITat 65° for 3 h
3. 3
   workup.ADDITIONThe reaction mixture was poured onto water
4. 4
   추출extracted with ethyl acetate
5. 5
   농축The solvent was concentrated
6. 6
   기타the crystalline impurity was removed by filtration
7. 7
   기타The filtrate was evaporated in vacuo
8. 8
   workup.DISSOLUTIONthe residue was dissolved in ethanol
9. 9
   온도heated
10. 10
    온도at reflux with hydrazine hydrate (2.5 ml) for 3 h
11. 11
    여과The mixture was filtered
12. 12
    workup.DISTILLATIONthe filtrate distilled

실험 절차

A mixture of 3-(1-piperidinylmethyl)phenol (8.7 g) and sodium hydride (1.2 g) in dimethylformamide (60 ml) was stirred at 25° during 3 h. N-(4-Bromobutyl)phthalimide (12.8 g) was added and the mixture was stirred at 25° during 20 h then at 65° for 3 h. The reaction mixture was poured onto water and extracted with ethyl acetate. The solvent was concentrated and the crystalline impurity was removed by filtration. The filtrate was evaporated in vacuo and the residue was dissolved in ethanol and heated at reflux with hydrazine hydrate (2.5 ml) for 3 h. The mixture was filtered and the filtrate distilled to give the title compound as a colourless oil (4.1 g) b.p. 140°/0.1 mm TLC silica, ethyl acetate/water/isopropanol/0.88 ammonia 25:8:15:2, Rf 0.32.

출처