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

HRID 358498
Notes
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Reaction equation

HRID 358498 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent
HCID 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-2ffd4ec607d641519f3b7bf60999cdc7
Source dataset
uspto-grants-1984_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04468402

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes