Ethyl Acetate → 7-Hydroxy-2-(4-hydroxy-phenyl)-3-{4-[2-(piperidin-1-yl)-ethoxy]-phenyl}-3H-quinazolin-4-one

HRID 617126Notes

Reaction equation

HRID 617126 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:7][CH:6]=1.C(O[CH2:34][CH3:35])(=O)C>N1CCCCC1>[OH:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:11]4[CH2:35][CH2:34][CH2:6][CH2:7][CH2:8]4)=[CH:6][CH:7]=3)[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)=[N:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 1358228303-[4-(2-Chloro-ethoxy)-phenyl]-7-hydroxy-2-(4-hydroxy-phenyl)-3H-quinazolin-4-one

Product 1

HCID 1355441217-Hydroxy-2-(4-hydroxy-phenyl)-3-{4-[2-(piperidin-1-yl)-ethoxy]-phenyl}-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution containing 0.25 g (0.000612 mol) of 3-[4-(2-chloro-ethoxy)-phenyl]-7-hydroxy-2-(4-hydroxy-phenyl)-3H-quinazolin-4-one in 7 mL of piperidine was stirred and heated to reflux for 2 hours. After cooling to room temperature, ethyl acetate was added to the reaction mixture and the solvents were co-evaporated to near dryness in a rotary evaporator. The dark residue was extracted with ethyl acetate and water. The aqueous layer was removed and chilled on ice. The precipitate which then formed was collected by vacuum filtration (0.052 g, mp 185-190° C.) and was shown to be the hydrochloride salt monohydrate.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customin a rotary evaporator
  4. extractionThe dark residue was extracted with ethyl acetate and water
  5. customThe aqueous layer was removed
  6. temperaturechilled on ice
  7. customThe precipitate which then formed
  8. filtrationwas collected by vacuum filtration (0.052 g, mp 185-190° C.)

Sources & evidence

ORD record
ord-9eb72418a59d4e4d8468e3a7f6857f09
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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