Sodium Chloride → 6-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril

HRID 1262851Notes

Reaction equation

HRID 1262851 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])[CH2:8][CH2:7]2)([OH:3])=O.ClC(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.[Cl-].[Na+]>CN(C)C=O.C(OCC)C.C(N(CC)CC)C>[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])[CH2:8][CH2:7]3)=[O:3])[CH2:32][CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 62365Isobutyl chloroformateHCID 759941-BenzylpiperazineHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 131953356-(4-Benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyrilYield 37.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 50 ml of dimethylformamide with 5.0 g of 6-carboxy-3,4-dihydrocarbostyril and 4 ml of triethylamine, 3.87 g of isobutyl chloroformate in 2 ml of dimethylformamide solution was added dropwise. After stirring at a room temperature for 30 minutes, 5.5 g of benzylpiperazine in 3 ml of dimethylformamide solution was added to the former solution and stirred at a room temperature for 30 minutes, then stirred continuously at 50°-60° C. for 1 hour. The reaction mixture was poured into a voluminous amount of a saturated sodium chloride aqueous solution and extracted with chloroform and the chloroform extract was washed with water and dried. After removal of the solvent, to the residue thus obtained was added diethyl ether to crystallize the residue and recrystallized from ethanol to obtain 3.4 g of 6-(4-benzyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril. Colorless needle-like crystals. Melting point: 198°-200° C.

Workup

  1. stirringstirred at a room temperature for 30 minutes
  2. stirringstirred continuously at 50°-60° C. for 1 hour
  3. extractionextracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with water
  6. customdried
  7. customAfter removal of the solvent
  8. customto the residue thus obtained
  9. customto crystallize the residue
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0a881a9924034524accfaf4fc1b5fb4c
Source dataset
uspto-grants-1984_06
Patent number
US04454130

Reaction notes

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