Isobutyl chloroformate → 6-(4-Benzyl-1-piperazinylcarbonyl)carbostyril monohydrochloride monohydrate

HRID 358497Notes

Reaction equation

HRID 358497 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]2)([OH:3])=[O:2].[Cl:15]C(OCC(C)C)=O.[CH2:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[OH2:2].[ClH:15].[CH2:23]([N:30]1[CH2:35][CH2:34][N:33]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]3)=[O:3])[CH2:32][CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 62365Isobutyl chloroformateHCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 133421682-Oxo-1,2-dihydroquinoline-6-carboxylic acid

Product 1

HCID 133698676-(4-Benzyl-1-piperazinylcarbonyl)carbostyril monohydrochloride monohydrate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

34.5 Grams of 6-carboxycarbostyril and 31 ml of triethylamine were dissolved in 350 ml of dimethylformamide and stirred at a room temperature. Then 28 ml of isobutyl chloroformate in 14 ml of dimethylformamide solution was added dropwise to the former solution. After stirring at a room temperature for 1 hour, 37 g of benzylpiperazine in 21 ml of dimethylformamide solution was added dropwise to the reaction mixture and stirred at a room temperature for 10 hours. The reaction mixture was poured into a saturated sodium bicarbonate aqueous solution, then extracted with chloroform. The chloroform layer was washed with water and a saturated sodium chloride aqueous solution in this order and the chloroform extract was dried with anhydrous sodium sulfate. The solvent was removed by distillation under a reduced pressure, the residue thus obtained was crystallized by adding ether and the crystals were collected by filtration. The crystals were dissolved in methanol and the pH of the solution was adjusted to about pH 1 by adding concentrated hydrochloric acid. The crude crystals thus obtained were recrystallized from ethanol-water to obtain 30.1 g of 6-(4-benzyl-1-piperazinylcarbonyl)carbostyril monohydrochloride monohydrate. Colorless granular crystals. Melting point: over 300° C.

Workup

  1. stirringAfter stirring at a room temperature for 1 hour
  2. stirringstirred at a room temperature for 10 hours
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. extractiona saturated sodium chloride aqueous solution in this order and the chloroform extract
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under a reduced pressure
  8. customthe residue thus obtained
  9. customwas crystallized
  10. additionby adding ether
  11. filtrationthe crystals were collected by filtration
  12. dissolutionThe crystals were dissolved in methanol
  13. additionby adding concentrated hydrochloric acid
  14. customThe crude crystals thus obtained
  15. customwere recrystallized from ethanol-water

Sources & evidence

ORD record
ord-c0fd0975bc7745a28f9105db97d32026
Source dataset
uspto-grants-1984_08
Patent number
US04468402

Reaction notes

Loading…