Water → HCID 19423587, compound

HRID 743067Notes

Reaction equation

HRID 743067 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:28])[CH2:8][CH2:7]1.[C:32](OC(=O)C)(=[O:34])[CH3:33].O>N1C=CC=CC=1>[C:32]([O:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([N:12]2[CH:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:28])[CH2:10][CH2:11]1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 19423546HCID 19423546, compound

Product 1

HCID 19423587HCID 19423587, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 207 mg (0.5 mmol) of 3-[1-(3-hydroxybenzyl)piperidin-4-yl]-4-phenyl-3,4-dihydro-2(1H)quinazolinone in 3 mL of pyridine was added 61 mg (0.6 mmol) of acetic anhydride, 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 water and then with brine, dried on sodium sulfate and then concentrated in vacuo. The residue was purified by means of column chromatography (silica gel, 1:9 methanol:chloroform) to give 187 mg (0.41 mmol) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer separated
  3. washwas washed with water
  4. dry with materialwith brine, dried 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-84f379aa54f84ff3a3c02087b36c0851
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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