Triethylamine → 8-[4-(2-Chlorobenzoyl)-1-piperazinyl]carbostyril

HRID 1649258Notes

Reaction equation

HRID 1649258 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[CH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>CN(C=O)C.C(=O)([O-])O.[Na+]>[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[NH:15][C:14](=[O:17])[CH:13]=[CH:12]3)[CH2:2][CH2:3]1)=[O:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 132363748-(1-Piperazinyl)carbostyril

Product 1

HCID 132363718-[4-(2-Chlorobenzoyl)-1-piperazinyl]carbostyrilYield 28.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent2×

Procedure

8-(1-Piperazinyl)carbostyril (0.7 g, 2.26 mmols) and sodium hydrogencarbonate (0.2 g) were suspended in 5 ml of DMF and the suspension was stirred at room temperature for 30 minutes. To the resulting mixture was added 0.4 ml of triethylamine, and further a solution of 0.47 g of 2-chlorobenzoyl chloride in 5 ml of DMF dropwise, followed by stirring at room temperature for 30 minutes. The reaction mixture was poured in saturated aqueous sodium hydrogencarbonate and extracted with chloroform. The organic layer was washed with water and then with saturated aqueous sodium hydrogencarbonate and dried over sodium sulfate. After distilling off the solvent, ether was added to the residue to crystallize. The crystals thus obtained were recrystallized from ethanol to give 0.24 g of 8-[4-(2-chlorobenzoyl)-1-piperazinyl]carbostyril, m.p. 239°-240.5° C., colorless needles.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated aqueous sodium hydrogencarbonate and dried over sodium sulfate
  5. distillationAfter distilling off the solvent, ether
  6. additionwas added to the residue
  7. customto crystallize
  8. customThe crystals thus obtained
  9. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-db40090d663b45f2b8040c7dac869dd9
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

Loading…