Piperidine → HCID 13377181, compound

HRID 1981901Notes

Reaction equation

HRID 1981901 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[CH2:14][CH:15]([CH3:16])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6]3.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CN1CCCC1=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[CH2:14][CH:15]([CH3:16])[N:7]3[C:8]=2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6]3

Participants

4

Reactant 2

HCID 8082PiperidineHCID 133771777-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Product 1

HCID 13377181HCID 13377181, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (0.5 g) and piperidine (0.8 g) are suspended in N-methylpyrrolidone (10 ml), and the mixture is heated at 110°-120° C. for 5 hours in a sealed tube. The reaction mixture is concentrated to dryness under reduced pressure, and to the residue is added ethyl acetate. The resulting crystals are separated by filtration and recrystallized from N,N-dimethylformamide to give 7-amino-8-fluoro-2-methyl-6-oxo-9-(1-piperidyl)-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (0.3 g) as yellow cubic crystals. m.p. 273°-276° C. (decomp.)

Workup

  1. temperaturethe mixture is heated at 110°-120° C. for 5 hours in a sealed tube
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. additionto the residue is added ethyl acetate
  4. customThe resulting crystals are separated by filtration
  5. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-1090f3f7a74e4022b3c77ba8557ca70c
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

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