Dabco → Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

HRID 1108665Notes

Reaction equation

HRID 1108665 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([CH:21]=1)[NH2:20].N12CCN(CC1)CC2>CS(C)=O.O>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:15]2[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([CH:21]=2)[NH2:20])[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 9237DabcoHCID 742185-Chloro-2-nitroanilineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22272542Tert-butyl 4-(3-amino-4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of t-butyl 1-piperazine carboxylate 38 (1.0 g., 5.4 mmole), 5-chloro-2-nitroaniline 54 (0.93 g., 5.4 mmole) and 1,4-diazabicyclo[2.2.2]octane (0.61 g., 54 mmole) in DMSO (10 mL.) was heated 16 hours under argon, cooled to r.t. and diluted with water (150 mL.) and extracted with ethyl acetate (3×50 mL.). The combined organic layers were washed with water (3×30 mL.) and dried over Na2SO4. Solvent was removed and the residue chromatographed (40% EtOAc/Hexane, silica) to give the title compound as a yellow solid, (0.5 g., 30%). MS (M+H)+ 323.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL.)
  2. washThe combined organic layers were washed with water (3×30 mL.)
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed
  5. customthe residue chromatographed (40% EtOAc/Hexane, silica)

Sources & evidence

ORD record
ord-d7dc02c89b3f4cbeb98a49afc3196e76
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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