Water → HCID 67449886, compound

HRID 1465816Notes

Reaction equation

HRID 1465816 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][C:12]=1[NH2:23])([O-:10])=[O:9].[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].O>CN(C=O)C>[CH3:24][N:25]([CH3:29])[C:26]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[C:12]([NH2:23])[CH:13]=2)[CH2:22][CH2:21]1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 602112HCID 602112, compound

Product 1

HCID 67449886HCID 67449886, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (0.546 g, 5.4 mmol) was added to 2-nitro-5-piperazin-1-yl-phenylamine (1.0 g, 4.5 mmol) in dry DMF (8 mL) and the mixture was cooled in an ice water bath. Dimethylcarbamyl chloride (0.581 g, 5.4 mmol) was added slowly to this reaction mixture via syringe and the mixture was brought up to room temperature and stirred overnight. After overnight stirring, the reaction mixture was slowly poured into cold water (100 mL) and stirred for 1 hour resulting in the solidification of the product. This was filtered, dried give the product, 4-(3-Amino-4-nitro-phenyl) -piperazine-1-carboxylic acid dimethylamide, as a yellow solid, 1.2 g (92.4% yield), which was used without any further purification.

Workup

  1. temperaturethe mixture was cooled in an ice water bath
  2. customwas brought up to room temperature
  3. stirringAfter overnight stirring
  4. stirringstirred for 1 hour
  5. customresulting in the solidification of the product
  6. filtrationThis was filtered
  7. customdried

Sources & evidence

ORD record
ord-d0c354364eb0440da9eaafcab7cab5e5
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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