반응 #456032

반응 방정식

n-butyllithium

hexane

diphenylphosphine

4-[2-(indan-1-yl)ethyl]-1-(4-methoxyphenyl)piperazine

4-[2-(Indan-1-yl)ethyl]-1-(4-methoxyphenyl)piperazine dihydrochloride

→

title compound

4-[2-(Indan-1-yl)ethyl]-1-(4-hydroxyphenyl)piperazine dihydrochloride

용매

THF

THF

반응 조건

후처리

1. 1
   온도The mixture is refluxed for 24 hr
2. 2
   기타quenched with water
3. 3
   추출extracted with ethyl acetate (2×800 ml)
4. 4
   세척The organic phase is washed with water, saline
5. 5
   건조dried (magnesium sulfate)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The concentrate is purified by liquid chromatography on silica gel 60 (230-400 mesh, 400 g)
9. 9
   세척eluting with hexane/acetone (2/1)
10. 10
    농축concentrated

실험 절차

A solution of diphenylphosphine (8.7 ml, 50 mmol) in THF (60 ml) is cooled to 0° under a nitrogen atmosphere and treated with n-butyllithium in hexane (1.6 M, 31.3 ml, 50 mmol). After stirring for 10 min, a solution of 4-[2-(indan-1-yl)ethyl]-1-(4-methoxyphenyl)piperazine (CXII, EXAMPLE 70, 6.73 g, 20 mmol) in THF (20 ml) is added. The mixture is refluxed for 24 hr, quenched with water and extracted with ethyl acetate (2×800 ml). The organic phase is washed with water, saline, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The concentrate is purified by liquid chromatography on silica gel 60 (230-400 mesh, 400 g), eluting with hexane/acetone (2/1). The appropriate fractions homogeneous by TLC are combined and concentrated to give the free base of the title compound. This free base is converted into the hydrochloric acid salt and recrystallized from ethyl acetate/methanol to give the title compound, mp 215-216°, NMR (DMSO-d6, TMS) 7.30-6.68 and 3.68-1.60 δ.

출처