1-(3-Chlorophenyl)piperazine → 6-{1-Oxo-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril

HRID 2291174Notes

Reaction equation

HRID 2291174 reaction equation
[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5]Cl.[I-].[Na+].[Cl:20][C:21]1[CH:22]=[C:23]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[O:1]=[C:2]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2)[CH2:3][CH2:4][CH2:5][N:30]1[CH2:29][CH2:28][N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 13551-(3-Chlorophenyl)piperazineHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Product 1

HCID 130648276-{1-Oxo-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

5.0 Grams of 6-(1-oxo-4-chlorobutyl)-3,4-dihydrocarbostyril and 7.5 g of sodium iodide were dispersed in 120 ml of anhydrous dimethylformamide and the mixture was stirred at 50°-60° C. for 2 hours. To this reaction mixture were added 10 g of 4-(3-chlorophenyl)piperazine and 5 ml of triethylamine and was stirred at 50°-60° C. for 6 hours, then stirred at a room temperature for 24 hours. The reaction mixture was concentrated under a reduced pressure to obtain a residue. To the residue thus obtained was added 80 ml of 5%-sodium hydrogencarbonate solution and the organic layer was extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation. The residue thus obtained was crystallized with ether to obtain crude crystals and the crude crystals were recrystallized from ethanol to obtain 6.5 g of 6-{1-oxo-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril in colorless needle-like crystals.

Workup

  1. stirringwas stirred at 50°-60° C. for 6 hours
  2. stirringstirred at a room temperature for 24 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. customto obtain a residue
  5. customTo the residue thus obtained
  6. extractionthe organic layer was extracted with chloroform
  7. washThe chloroform layer was washed with water
  8. customdried
  9. customchloroform was removed by distillation
  10. customThe residue thus obtained
  11. customwas crystallized with ether
  12. customto obtain crude crystals
  13. customthe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-3e518598b3c149e1add63360534fd9e8
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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