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ChemicalBook CAS DataBase List 1-(2-CHLORO-6-NITROPHENYL)PIPERAZINE

1-(2-CHLORO-6-NITROPHENYL)PIPERAZINE synthesis

3synthesis methods
-

Yield:332023-12-8 95%

Reaction Conditions:

in dichloromethane;trifluoroacetic acid;

Steps:

17.B 1-[3-Chloro-2-(4-{3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propyl}-piperazin-1-yl)-phenyl]-urea.

B. 1-(2-chloro-6-nitro-phenyl)-piperazine. 4-(2-Chloro-6-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.87 g, 5.47 mmol) was dissolved in trifluoroacetic acid (5.0 mL) and CH2Cl2 (5.0 mL) and allowed to stir for 2 h. The reaction mixture was concentrated, diluted with EtOAc, and washed with saturated aq. NaHCO3. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (silica, 100% CH2Cl2) to afford 1-(2-chloro-6-nitro-phenyl)-piperazine (1.26 g, 95%). MS (electrospray): exact mass calculated for C10H12ClN3O2, 241.1; m/z found, 242.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.54 (dd, J=8.2, 1.6 Hz, 1H), 7.49 (dd, J=8.2, 1.6 Hz, 1H), 7.10 (t, J=8.2 Hz, 1H), 3.08 (br s, 4H), 2.99 (br s, 4H), 2.07-2.12 (m, 1H).

References:

US2003/69240,2003,A1