Dimethylformamide → HCID 53923744, compound

HRID 342549Notes

Reaction equation

HRID 342549 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1([CH:17]=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CN(C=O)C>O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:14]1[CH2:15][CH2:16][N:11]([CH:17]=[O:18])[CH2:12][CH2:13]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69451-Chloro-2-nitrobenzeneHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 53923744HCID 53923744, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-chloro-2-nitrobenzene (6.54 g, 41.5 mmol), piperazine-1-carboxaldehyde (4.7 g, 41.5 mmol) and DMF (18 mL) was heated 48 hours at 100° C. The reaction mixture then was cooled, diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with water, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (98:2) to give 4-(2-nitrophenyl)piperazine-1-carbaldehyde (3.2 g, 13.7 mmol).

Workup

  1. temperatureThe reaction mixture then was cooled
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (98:2)

Sources & evidence

ORD record
ord-36f732ac02d24672abe2b21cf3001c9f
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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