Reaktion #467724

Reaktionsgleichung

1-benzylpiperidin-4-one

1-bromonaphthalene

sec-butyllithium

→

desired compound

Ausbeute 32.4%

1-benzyl-4-hydroxy-4-(naphth-1-yl)piperidine

Ausbeute 32.4%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was then quenched by the addition of 2 N sodium hydroxide
2. 2
   ExtraktionThe resulting mixture was extracted with diethyl ether
3. 3
   Waschenwashed with saturated aqueous sodium chloride
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Wascheneluting with dichloromethane containing from 0 to 2% methanol
6. 6
   workup.ADDITIONFractions containing product
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of 10.0 gm (42.2 mMol) 1-bromonaphthalene in 180 mL tetrahydrofuran was cooled to −78° C. and then to this solution were added 48.7 mL (63.3 mMol) sec-butyllithium (1.3 M in cyclohexane). After stirring for about 1.5 hours, a solution of 8.2 mL (44.3 mMol) 1-benzylpiperidin-4-one in 60 mL tetrahydrofuran was added dropwise and the resulting mixture was allowed to warm gradually to room temperature. The reaction was then quenched by the addition of 2 N sodium hydroxide. The resulting mixture was extracted with diethyl ether. The organic extracts were combined, washed with saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 0 to 2% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 4.34 gm (32%) of the desired compound as a white foam.

Quelle