Piperidine → HCID 9839546, compound

HRID 2270268Notes

Reaction equation

HRID 2270268 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](F)[CH:17]=2)[C:12](=[O:21])[N:11]([OH:22])[C:10]1=[O:23])[CH3:8].C(N(CC)CC)C>C(#N)C>[CH2:7]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:17]=2)[C:12](=[O:21])[N:11]([OH:22])[C:10]1=[O:23])[CH3:8]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 15908877HCID 15908877, compound

Product 1

HCID 9839546HCID 9839546, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperidine (0.025 mL, 0.22 mmol) was added to a solution of 1-ethyl-6,7-difluoro-3-hydroxy-1H-quinazoline-2,4-dione (Example D, 0.05 g, 0.2 mmol) and triethylamine (0.06 mL, 0.4 mmol) in 20 mL of acetonitrile. The solution was heated to reflux for 23 hours, cooled, and concentrated to a solid. The solid was dissolved in chloroform washed with 1N HCl, water, brine, and dried over magnesium sulfate. The solution was concentrated to give 0.03 g of the title compound as a solid, mp 173-175° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 23 hours
  3. temperaturecooled
  4. concentrationconcentrated to a solid
  5. dissolutionThe solid was dissolved in chloroform
  6. washwashed with 1N HCl, water, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-13372bb2cd8b433485859a65ac6b70f9
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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