Benzyl Chloride → HCID 12944896, compound

HRID 544224Notes

Reaction equation

HRID 544224 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:19])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:19])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 30516953-Quinolinecarboxylic acid, 1,4-dihydro-6-chloro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 12944896HCID 12944896, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6-chloro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 1.7 g (0.005 mole), benzylchloride 1.26 g (0.01 mole), triethylamine (0.01 mole) and DMF 10 ml was heated at 90°-100° C. for 7 hours under stirring. After cooling, the reaction mixture was dried up under vacuum. The residue was dissolved in CHCl3, washed with water, dried with anhydrous Na2SO4, and the solvent was distilled off. The residue was recrystallized from a mixed solvent of DMF and ethanol to obtain 1.1 g (52%) of 1-ethyl-6-chloro-7-(4-benzyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Colorless prism.

Workup

  1. temperaturewas heated at 90°-100° C. for 7 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was dried up under vacuum
  4. dissolutionThe residue was dissolved in CHCl3
  5. washwashed with water
  6. dry with materialdried with anhydrous Na2SO4
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from a mixed solvent of DMF and ethanol

Sources & evidence

ORD record
ord-4a5592b80f9f4441b6a73b05c0f4f08b
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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