Piperidin-4-ol → HCID 13588382, compound

HRID 1981902Notes

Reaction equation

HRID 1981902 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.[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN1CCCC1=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:25]2[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]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 79341Piperidin-4-olHCID 133771777-Amino-8,9-difluoro-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid

Product 1

HCID 13588382HCID 13588382, compoundYield 31%

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 4-hydroxypiperidine (1.0 g) are suspended in N-methylpyrrolidone (5 ml), and the mixture is heated at 110°-120° C. for 5 hours. The reaction mixture is concentrated to dryness under reduced pressure, and to the residue is added ethanol. The resulting crystals are separated by filtration and recrystallized from N,N-dimethylformamide to give 7-amino-8-fluoro-9-(4-hydroxy-1-piperidyl)-2-methyl-6-oxo-1,2-dihydro-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid (0.2 g) as yellow cubic crystals. m.p. 287°-292° C. (decomp.)

Workup

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

Sources & evidence

ORD record
ord-7f4d58ed4c1e497dac6569dc1703bb2b
Source dataset
uspto-grants-1986_06
Patent number
US04594347

Reaction notes

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