Piperazine → HCID 14651228, compound

HRID 1081431Notes

Reaction equation

HRID 1081431 reaction equation
[F:1][C:2]1[C:3]([CH3:22])=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([CH:14]=[CH2:15])[CH:7]=[C:6]([C:16]([O:18]CC)=[O:17])[C:5]2=[O:21].[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(#N)C>>[F:1][C:2]1[C:3]([CH3:22])=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[N:8]([CH:14]=[CH2:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:21]

Participants

4

Reactant 3

HCID 4837PiperazineHCID 6342AcetonitrileHCID 14651281HCID 14651281, compound

Product 1

HCID 14651228HCID 14651228, compoundYield 50.9%

Conditions

Temperature
80 °C

Procedure

A solution of 0.69 g (1.80 mmol) of ethyl 6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-1-vinyl-3-quinolinecarboxylate, 0.62 g (7.2 mmol) of anhydrous piperazine, and 20 mmol of acetonitrile was refluxed for 18 hours, cooled, and concentrated. The residue was suspended in 25 mL of 1N sodium hydroxide and heated at 80° C. for 90 minutes. The clear yellow solution was cooled to room temperature, filtered, and neutralized (pH 6.8) with 6N hydrochloric acid. The solids were filtered, washed with water and ether, and dried to give 0.32 g of the title compound, mp 222°-225° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. temperatureThe clear yellow solution was cooled to room temperature
  4. filtrationfiltered
  5. filtrationThe solids were filtered
  6. washwashed with water and ether
  7. customdried

Sources & evidence

ORD record
ord-5e8d524099984b779756e98a36114ab3
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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