Dichloromethane → 1-(2-Chloro-6-nitrophenyl)piperazine

HRID 132913Notes

Reaction equation

HRID 132913 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:23])[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)Cl>FC(F)(F)C(O)=O>[Cl:23][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 587677041-Boc-4-(2-chloro-6-nitrophenyl)piperazine

Product 1

HCID 27714081-(2-Chloro-6-nitrophenyl)piperazineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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 C10H12CIN3O2, 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).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated aq. NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica, 100% CH2Cl2)

Sources & evidence

ORD record
ord-e9f59b15480346b1b3393c5cdd16d34b
Source dataset
uspto-grants-2008_06
Patent number
US07388011B2

Reaction notes

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