Water → HCID 9799043, compound

HRID 479456Notes

Reaction equation

HRID 479456 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:23])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH:32]1[CH2:34][CH2:33]1.O>CN(C)C=O>[CH:32]1([CH2:31][N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[CH:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]3=[O:23])[CH2:5][CH2:6]2)[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 15896329HCID 15896329, compound

Product 1

HCID 9799043HCID 9799043, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 200 mg (0.65 mmol) of 3-(piperidin-4-yl)-4-phenyl-3,4-dihydro-2(1H)-quinazolinone in 5 ml of N,N-dimethylformamide (DMF), 270 mg (1.95 mmol) of potassium carbonate and 176 mg (1.30 mmol) of bromomethylcyclopropane were added at room temperature subsequently and stirred at about 50° C. for 5 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to afford a residue, which was purified by silica gel column chromatography (chloroform—10% methanol/chloroform) to give 231 mg (0.64 mmol) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customto afford a residue, which
  6. customwas purified by silica gel column chromatography (chloroform—10% methanol/chloroform)

Sources & evidence

ORD record
ord-ff4991a2a1804065bc8bbc864ea4bd8c
Source dataset
uspto-grants-2003_11
Patent number
US06645971B1

Reaction notes

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