Reaction #11769

Reaction equation

2,5-dichloro-3-nitro-pyridine

1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-hydroxy-ethanone

sodium hydride

→

title compound

Yield 78.3%

2-(5-Chloro-3-nitro-pyridin-2-yloxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

Yield 78.3%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at ambient temperature overnight
2. 2
   OtherThe, reaction
3. 3
   Concentrationwas concentrated
4. 4
   Otherchromatographed on silica gel

Procedure

To a solution of 1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-2-hydroxy-ethanone (0.77 g, 2.9 mmol) in dry toluene (30 mL) at 0° C. was added sodium hydride (0.13 g, 3.2 mmol, 60% dispersion in mineral oil). The reaction was stirred for 30 minutes at 0° C. followed by addition of 2,5-dichloro-3-nitro-pyridine (0.60 g, 3.18 mmol) as a solution in toluene (5 mL). The reaction was stirred at ambient temperature overnight. The, reaction was concentrated and chromatographed on silica gel to give the title compound (0.96 g).

Source