1-Isopropylpiperazine → HCID 13960247, compound

HRID 2413969Notes

Reaction equation

HRID 2413969 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH2:15][CH3:16])[CH:11]=[CH:12]2)[CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6](=[O:20])[C:5]3=[CH:4][C:3]=1[F:21].[CH:22]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([CH3:24])[CH3:23]>CS(C)=O>[F:21][C:3]1[CH:4]=[C:5]2[C:14]3[N:9]([CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6]2=[O:20])[CH:10]([CH2:15][CH3:16])[CH:11]=[CH:12][C:13]=3[C:2]=1[N:28]1[CH2:29][CH2:30][N:25]([CH:22]([CH3:24])[CH3:23])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 780131-IsopropylpiperazineHCID 20154356HCID 20154356, compound

Product 1

HCID 13960247HCID 13960247, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.62 g (0.015 mole) of 8-chloro-9-fluoro-5-ethyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid was suspended in 45 ml of dimethyl sulfoxide, 7.69 g (0.06 mole) of N-isopropylpiperazine was added thereto, and this mixture was stirred at 100°-110° C. for 8 hours. The resulting reaction solution was evaporated to dryness under reduced pressure. 40 ml of methanol was added to the resulting residue and this mixture was stirred. The insoluble matter was collected by filtration and recrystallized from ethanol to obtain 3.88 g (64.7% yield) of 9-fluoro-5-ethyl-8-(4-isopropyl-1-piperazinyl)-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in the form of pale-yellow crystals. These crystals had a melting point of 186°-195° C. (dec.).

Workup

  1. customThe resulting reaction solution
  2. customwas evaporated to dryness under reduced pressure
  3. addition40 ml of methanol was added to the resulting residue
  4. stirringthis mixture was stirred
  5. filtrationThe insoluble matter was collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1e10050a102a402fafead9d936776bb2
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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