Water → HCID 19423543, compound

HRID 743065Notes

Reaction equation

HRID 743065 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:38]=[CH:39][CH:40]=1)[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:37])[CH2:17][CH2:16]1)=[O:10])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:1][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:38]=[CH:39][CH:40]=1)[CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([N:21]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:37])[CH2:19][CH2:20]1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 19423564HCID 19423564, compound

Product 1

HCID 19423543HCID 19423543, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 300 mg (0.56 mmol) of 3-[1-(3-benzyloxycarbonylbenzyl)piperidin-4-yl]-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 20 mL of methanol was added 8 mg (0.06 mmol) of potassium carbonate and the mixture was stirred for 12 hours at ambient temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer separated was washed with brine, dried on sodium sulfate and concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 179 mg (0.39 mmol) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer separated
  3. washwas washed with brine
  4. customdried on sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform)

Sources & evidence

ORD record
ord-a3960b6dbc684c3bb7cc9af0f6d1397a
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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