2,4,6-Trichloronitrobenzene → HCID 66854794, compound

HRID 2400766Notes

Reaction equation

HRID 2400766 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=2[N+:10]([O-:12])=[O:11])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 292282,4,6-TrichloronitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 66854794HCID 66854794, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,3,5-trichloronitrobenzene (800 mg) and 1-t-butoxycarbonyl-piperazine (790 mg) in toluene (20 ml) was stirred at 80° C. under N2 for 15 hours. The reaction mixture was cooled to room temperature, partitioned between water and ethyl acetate, the organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was subjected to silica gel chromatography (cyclohexane:ethyl acetate 8:2) to afford 4-(3,5-dichloro-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.37 g). 1H NMR (400 MHz, CDCl3) 1.5 (s, 9H), 2.9 (m, 4H), 3.5 (m, 4H), 7.0 (d, J=2 Hz, 1H), 7.16 (d, J=2 Hz, 1H); Retention Time HPLC 2.33 min; MS (ES+) 276/278 (M-BOC), 317/319 (M-isoprene).

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f2d2a833ab3467a8c58a5f38d987a32
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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