Piperazine → HCID 14128502, compound

HRID 621574Notes

Reaction equation

HRID 621574 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=[O:16])[NH:11]2.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>>[N:17]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH2:8][CH2:9][C:10](=[O:16])[NH:11]3)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 12899139HCID 12899139, compound

Product 1

HCID 14128502HCID 14128502, compoundYield 49.7%

Procedure

(a)-1 3.0 grams of 5-(3-chloropropoxy)-3,4-dihydrocarbostyril and 10 g of piperazine are mixed with 20 ml of hexamethylphosphoryl triamide and heated at 80°-90° C. for 5 hours. The reaction mixture is distilled under a reduced pressure to remove hexamethylphosphoryl triamide and unreacted piperazine. To the residue thus obtained are added 30 ml of 5%-NaHCO3 aqueous solution, followed by extraction with chloroform. The chloroform layer is washed with water and chloroform is removed by distillation. The residue thus obtained is purified by silica-gel chromatography to obtain 1.8 g of 5-(3-piperazinylpropoxy)-3,4-dihydrocarbostyril having a melting point of 192°-195° C.

Workup

  1. temperatureheated at 80°-90° C. for 5 hours
  2. distillationThe reaction mixture is distilled under a reduced pressure
  3. customto remove hexamethylphosphoryl triamide and unreacted piperazine
  4. customTo the residue thus obtained
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform layer is washed with water and chloroform
  7. customis removed by distillation
  8. customThe residue thus obtained
  9. customis purified by silica-gel chromatography

Sources & evidence

ORD record
ord-43e9f53517924ca99085d57bf35da754
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

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