Reaction #88873

Reaction equation

2,4′-bipyridine-3-carboxylic acid dihydrochloride

4-benzyl-4-hydroxypiperidine

HATU

triethylamine

→

title compound

Yield 46.8%

(4-benzyl-4-hydroxypiperidin-1-yl)(2,4′-bipyridin-3-yl)methanone

Yield 46.8%

Solvents

water

DMF

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   WashThe extract was washed with saturated brine
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   OtherThe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
6. 6
   Otherrecrystallized from ethyl acetate/hexane

Procedure

A suspension of 2,4′-bipyridine-3-carboxylic acid dihydrochloride (5.0 g), 4-benzyl-4-hydroxypiperidine (3.9 g), HATU (10 g) and triethylamine (13 mL) in DMF (50 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and recrystallized from ethyl acetate/hexane to give the title compound (3.2 g).

Source