Reaktion #54757

Reaktionsgleichung

phenethyl bromide

sodium hydride

pentane

4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

→

N-Phenethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Lösungsmittel

dimethylformamide

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 50° under nitrogen
2. 2
   TemperaturThe mixture was heated at 90° for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   Temperaturthe reaction mixture heated at 90° overnight
5. 5
   Extraktionextracted with ether
6. 6
   SonstigeEvaporation of the ether
7. 7
   Sonstigegave an oil which
8. 8
   Sonstigewas purified by column chromatography (Silicar CC-7, eluting with acetone-benzene)

Vorschrift

A solution of 10.0 g (37 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 250 ml of anhydrous dimethylformamide was added with stirring to a suspension of 2.8 g (55.5 mmoles) of 50% sodium hydride in mineral oil (washed with pentane) in 125 ml of anhydrous dimethylformamide heated at 50° under nitrogen. The mixture was heated at 90° for 2 hours, then cooled to 40°, at which time a solution of 14.0 g (74 mmoles) of phenethyl bromide in 20 ml of anhydrous dimethylformamide was added and the reaction mixture heated at 90° overnight. The cooled solution was poured into ice-water and extracted with ether. Evaporation of the ether gave an oil which was purified by column chromatography (Silicar CC-7, eluting with acetone-benzene). The major fraction was identified as N-phenethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline.

Quelle