2-Chloro-1-fluoro-4-nitrobenzene → Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylate

HRID 1108664Notes

Reaction equation

HRID 1108664 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:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F.C(N(C(C)C)CC)(C)C>CS(C)=O>[Cl:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18783805Tert-butyl 4-(2-chloro-4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of t-butyl 1-piperazinecarboxylate 38 (1.0 g., 5.37 mmole), 3-chloro-4-fluoronitrobenzene (0.94 g., 5.37 mmole) and diisopropylethylamine (0.70 g., 5.4 mmole) in DMSO (30 mL.) was heated 16 hours at 100°, cooled to r.t. and poured into ice water (300 mL.). The suspension was extracted with ethyl acetate (2×60 mL.). The combined organic layers were washed with water (3×40 mL.), dried over Na2SO4 and evaporated to dryness to give an orange solid which was recrystallized twice from methanol to give the title compound, 1.2 g. MS (M+H)+ 342.0

Workup

  1. extractionThe suspension was extracted with ethyl acetate (2×60 mL.)
  2. washThe combined organic layers were washed with water (3×40 mL.)
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customto give an orange solid which
  6. customwas recrystallized twice from methanol

Sources & evidence

ORD record
ord-f956887961a84d16a17c025cf5b997bb
Source dataset
uspto-grants-2000_05
Patent number
US06069143

Reaction notes

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