Reaktion #456032

Reaktionsgleichung

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is refluxed for 24 hr
2. 2
   Sonstigequenched with water
3. 3
   Extraktionextracted with ethyl acetate (2×800 ml)
4. 4
   WaschenThe organic phase is washed with water, saline
5. 5
   Trocknendried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe concentrate is purified by liquid chromatography on silica gel 60 (230-400 mesh, 400 g)
9. 9
   Wascheneluting with hexane/acetone (2/1)
10. 10
    Einengenconcentrated

Vorschrift

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.

Quelle