Ethyl bromoacetate → HCID 19423555, compound

HRID 743061Notes

Reaction equation

HRID 743061 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:23])[CH2:3][CH2:2]1.Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.[I-].[K+]>[CH2:29]([O:28][C:26]([CH2:25][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:23])[CH2:5][CH2:6]1)=[O:27])[CH3:30]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15896329HCID 15896329, compound

Product 1

HCID 19423555HCID 19423555, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 1.5 g (4.88 mmol) of 3-(piperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 30 mL of isopropanol were added 896 mg (5.37 mmol) of ethyl bromoacetate, 853 mg (96.18 mmol) of potassium carbonate and 20 mg of potassium iodide, and the mixture was heated under reflux for 3 hours. The hot solution was subjected to filtration, and the solid matter was washed with 200 mL of hot isopropanol. The filtrate was concentrated in vacuo, and the residue was purified by means of column chromatography (silica gel, 1:9 :90 aqueous ammonia:methanol:chloroform) to give 1.88 g (4.37 mmol) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe hot solution was subjected to filtration
  4. washthe solid matter was washed with 200 mL of hot isopropanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by means of column chromatography (silica gel, 1:9 :90 aqueous ammonia:methanol:chloroform)

Sources & evidence

ORD record
ord-59451cfdf48c49248701f3133e7a83dc
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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