Hydrochloric Acid → HCID 13377054, compound

HRID 745659Notes

Reaction equation

HRID 745659 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl.[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1)([O-:29])=[O:28].C(N(CC)CC)C>CN(C)C=O>[N+:27]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][N:23]2[CH2:22][CH2:21][N:20]([C:3]3[C:4]4=[C:13]5[N:8]([CH:7]([CH3:19])[CH2:6][CH2:5]4)[CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11](=[O:15])[C:12]5=[CH:14][C:2]=3[F:1])[CH2:25][CH2:24]2)=[CH:32][CH:31]=1)([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 15571787HCID 15571787, compound

Product 1

HCID 13377054HCID 13377054, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-fluoro-6,7-dihydro-5-methyl-8-(1-piperazinyl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid (Compound [III]), hydrochloride (1.1 g), p-nitrobenzyl bromide (Compound [IV]) (1.87 g) and triethylamine (1.46 g) in N,N-dimethylformamide (50 ml) was heated with stirring at 80°-90° C. for 10 hr. After evaporation of the solvent, water was added to the residue, and the aqueous mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was recrystallized from a mixture of N,N-dimethylformamide and ethanol (2:1) to give 0.83 g (yield: 60%) of 8-[4-(4-nitrobenzyl)-1-piperazinyl]-9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid (Compound [II]) as pale yellow needles, m.p. 230°-233° C. (decompd.).

Workup

  1. temperaturewas heated
  2. customAfter evaporation of the solvent, water
  3. additionwas added to the residue
  4. extractionthe aqueous mixture was extracted with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was recrystallized from a mixture of N,N-dimethylformamide and ethanol (2:1)

Sources & evidence

ORD record
ord-0208913166824fd3b3cff771bf82c585
Source dataset
uspto-grants-1986_07
Patent number
US04599418

Reaction notes

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