Ammonia → 2-Piperazin-1-yl-benzamide

HRID 276892Notes

Reaction equation

HRID 276892 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)#[N:2].N.S(=O)(=O)(O)[OH:17]>>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)(=[O:17])[NH2:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 106558542-Piperazin-1-yl-benzamide

Procedure

1-(2-Cyanophenyl)piperazine (1.8 g, 9.8 mmol) was dissolved in 90% sulfuric acid aqueous solution (20 ml) and stirred at a room temperature for 24 hours. The reaction solution was slowly added dropwise to a mixture of ice (75 g) and 28% aqueous ammonia (75 ml), and the reaction product was extracted with chloroform. The extract was washed with saturated brine and dried with sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated by an aluminum column chromatography to obtain colorless crystals. By further recrystallizing the thus obtained crystals from ethyl acetate, 680 mg of the title compound was obtained (3.1 mmol, 32% in yield).

Workup

  1. extractionthe reaction product was extracted with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialdried with sodium sulfate
  4. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  5. customwas separated by an aluminum column chromatography
  6. customto obtain colorless crystals
  7. customBy further recrystallizing the thus obtained crystals from ethyl acetate

Sources & evidence

ORD record
ord-de76be4ed8d3435bb3264cc36190c0e7
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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