Benzoyl chloride, 3-nitro- → (4-Methylpiperazin-1-yl)(3-nitrophenyl)methanone

HRID 1487150Notes

Reaction equation

HRID 1487150 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C1COCC1.O>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:8])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 531671-Methylpiperazine

Product 1

HCID 763411(4-Methylpiperazin-1-yl)(3-nitrophenyl)methanoneYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-nitrobenzoyl chloride (4.5 g, 24.25 mmol) in THF (30 ml) was added 1-methylpiperazine (8.50 g, 85 mmol). The reaction was stirred for 20 min at room temperature. The reaction mixture was diluted with 50 mL water and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with brine (50 mL). The brine was back extracted with ethyl acetate (2×50 mL) and all the organic layers were combined, dried over magnesium sulphate, filtered, and concentrated under vacuum give the title product (5.2 g).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic layer was washed with brine (50 mL)
  3. extractionThe brine was back extracted with ethyl acetate (2×50 mL) and all the organic layers
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-527177e999374add81098adf56dd4054
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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