Piperidine → 6,7-Difluoroquinazolin-4(3H)-one

HRID 353159

Reaction equation

HRID 353159 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH:13]1CCCC[CH2:14]1.N1C=NC=NC=1>C(O)C>[F:12][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[F:11])[N:1]=[CH:14][NH:13][C:4]2=[O:5]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 92621,3,5-TriazineHCID 7359652-Amino-4,5-difluorobenzoic acid

Product 1

HCID 1354713086,7-Difluoroquinazolin-4(3H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.81 g (27.8 mmol) of commercially available 2-amino-4,5-difluorobenzoic acid in 20 ml of ethanol were added 1.92 ml (19.4 mmol) of piperidine and 2.25 g (27.8 mmol) of 1,3,5-triazine, followed by heating under reflux in an atmosphere of argon for 6.5 hours. After the reaction mixture was allowed to cool to room temperature, the solvent was evaporated. To the residue was added water, and the resulting mixture was neutralized with 4 N hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and dried to give 4.37 g (86%) of 6,7-difluoro-4(3H)-quinazolone.

Workup

  1. temperatureby heating
  2. temperatureunder reflux in an atmosphere of argon for 6.5 hours
  3. customthe solvent was evaporated
  4. additionTo the residue was added water
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-26367b7bf5f44bffb86b8d2214bf5dda
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Linked notes

Loading…