Water → HCID 9847503, compound

HRID 479459Notes

Reaction equation

HRID 479459 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:29])[CH2:9][CH2:8]1.[H-].[Na+].Br[CH2:36][CH2:37][CH3:38].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:36]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:13]([CH:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:30]=[CH:31][CH:32]=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH2:8][CH2:9]2)[C:14]1=[O:29])[CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 15896333HCID 15896333, compound

Product 1

HCID 9847503HCID 9847503, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.234 mmol) of 3-[1-(3-hydroxymethylbenzyl) piperidin-4-yl]-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 2 ml of DMF, 11.2 mg (0.28 mmol) of sodium hydride (60%) were added under ice-cooling and stirred at the same temperature for 5 minutes and at room temperature for 5 minutes. After ice-cooling again, 0.032 ml (0.35 mmol) of 1-bromopropane was added thereto and stirred under ice-cooling for 3 hours and at room temperature for 6 hours. To the reaction mixture, 2 mg of tetrabutylammonium iodide were added and further stirred at room temperature for 5 hours. It was poured into water, extracted with ethyl acetate, washed with water, aqueous saturated sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform—2% methanol/chloroform) to give 47 mg (0.10 mmol) of the title compound as colorless oil.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling again
  3. stirringstirred under ice-
  4. temperaturecooling for 3 hours and at room temperature for 6 hours
  5. stirringfurther stirred at room temperature for 5 hours
  6. extractionextracted with ethyl acetate
  7. washwashed with water, aqueous saturated sodium bicarbonate solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter the solvent was evaporated under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (chloroform—2% methanol/chloroform)

Sources & evidence

ORD record
ord-d1dcc9a96fa745569ec14064d2bceb06
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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