1,2-Dichloro-4-nitrobenzene → HCID 7059976, compound

HRID 1971232Notes

Reaction equation

HRID 1971232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.[CH3:12][C@H:13]1[CH2:18][NH:17][CH2:16][C@@H:15]([CH3:19])[NH:14]1.C(N(CC)CC)C>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:17]1[CH2:16][C@H:15]([CH3:19])[NH:14][C@H:13]([CH3:12])[CH2:18]1

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 8471TriethylamineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 7059976HCID 7059976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (5.21 mmol) of 3,4-dichloronitrobenzene (Fluka, Buchs, Switzerland), 624 mg (5.47 mmol) cis-2,6-dimethylpiperazine (Aldrich, Buchs, Switzerland) and 580 mg (5.73 mmol) triethylamine in 20 ml of EtOH are heated in a microwave oven at 170° C. for 6 h and 180° C. for 2 h. The reaction mixture is evaporated to dryness and then taken in EtOAc. The organic layers is extracted with 1 M aqueous HCl(5×) and the combined aqueous layers are basified with NaHCO3 and extracted with CH2Cl2 (3×), washed with brine, dried over MgSO4, filtered and evaporated to dryness to give the title compound as a yellow solid. ES-MS: 270 (M+H)+; analytical HPLC: tret=2.72 minutes (Grad 1).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. extractionThe organic layers is extracted with 1 M aqueous HCl(5×)
  3. extractionextracted with CH2Cl2 (3×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e0224ad072f14ec6866abce6311ac5c7
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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