Ammonia → HCID 19423622, compound

HRID 743068Notes

Reaction equation

HRID 743068 reaction equation
Cl.[CH3:2][S:3][C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:30])[CH2:10][CH2:9]1.ClC1C=CC=C(C(OO)=[O:42])C=1.O.N>C(Cl)Cl>[CH3:2][S:3]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:30])[CH2:12][CH2:13]1)=[O:42]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 67626345HCID 67626345, compound

Product 1

HCID 19423622HCID 19423622, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 480 mg (1 mmol) of 3-[1-(3-methylthiobenzyl)piperidin-4-yl]-4-phenyl-3,4-dihydro -2(1H)-quinazolinone HCl salt in 10 mL of methylene chloride was added 190 mg (1.1 mmol) of m-chloroperbenzoic acid at temperature of 0° C. to 10° C. The mixture was stirred for 10 hours at ambient temperature, mixed with water, adjusted to pH 10 with a aqueous ammonia and then extracted with chloroform. The organic layer separated was washed 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 440 mg (0.96 mmol) of the title compound as an about 1:1 mixture of the diastereomers.

Workup

  1. extractionextracted with chloroform
  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-f2fee59fe3f243a0807af8cb574b5ebc
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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