Diisopropylethylamine → Piperazine, 1-cyclopentyl-4-(4-nitro-2-pyridinyl)-

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.6 g (35 mmol) 2-chloro-4-nitropyridine, 5.75 g (37 mmol) 1-cyclo-pentyl piperazine and 4.59 g (35 mmol) N,N-diisopropylethylamine in 35 ml DMF and 12 ml water was heated to 95° C. for 3 h. After evaporation to dryness the residue was taken up in 150 ml NaHCO3 aq. and 150 ml ethyl acetate. The aqueous phase was extracted two times with 150 ml ethyl acetate each and the combined organic phases were washed twice with 100 ml NaHCO3 aq each and 100 ml NaCl aq. sat. and dried with MgSO4 and evaporated to dryness. The residue was purified with column chromatography to yield 2.85 g (29%) 1-cyclopentyl-4-(4-nitro-pyridin-2-yl)-piperazine (m/e): 277.3 (MH+; 100%) and 4.47 g (47%) 1-(2-chloro-pyridin-4-yl)-4-cyclopentyl-piperazine (m/e): 266.3 (MH+; 100%).

Provenance & Evidence