Reaction #546965

Reaction equation

1-BOC-piperizine

2,6-dinitrobenzonitrile

water ethyl acetate

→

4-(2-cyano-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Yield 69.0%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was cooled to room temperature
2. 2
   WashThe organic fraction was washed with water and brine
3. 3
   DryingAfter drying over MgSO4
4. 4
   Concentrationthe organic fraction was concentrated in vacuo
5. 5
   Otherthe resulting brown residue was purified by flash chromatography

Procedure

1-BOC-piperizine (piperazine-1-carboxylic acid tert-butyl ester, 20.0 g, 107.4 mmol) was added to a solution of 2,6-dinitrobenzonitrile (10.277 g, 53.2 mmol) in dry DMF (200 ml). After stirring at 50° C. overnight, the reaction mixture was cooled to room temperature and poured into a mixture of water/ethyl acetate. The organic fraction was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and the resulting brown residue was purified by flash chromatography to give 4-(2-cyano-3-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as an orange solid (12.172 g, 69%). MS: (M+H)+277.1.

Source