Iodoethane → HCID 11537851, compound

HRID 2111832Notes

Reaction equation

HRID 2111832 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)[C:10](=[O:25])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:26](I)[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:26]([N:22]1[CH2:23][CH2:24][CH:19]([O:18][C:15]2[CH:14]=[CH:13][C:12]([N:11]3[C:10](=[O:25])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]3[CH3:1])=[CH:17][CH:16]=2)[CH2:20][CH2:21]1)[CH3:27]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 23151166HCID 23151166, compound

Product 1

HCID 11537851HCID 11537851, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-methyl-3-[4-(4-piperidinyloxy)phenyl]-4(3H)-quinazolinone (50 mg, 0.15 mmol), ethyl iodide (23 mg, 0.15 mmol) and potassium carbonate (0.30 mmol) were mixed in dimethylformamide (1 mL), and stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, ethyl acetate and 1N sodium hydroxide aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with distilled water, dried with anhydrous sodium sulfate, and the product was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain the title compound (25 mg, 46%) as a colorless solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate and 1N sodium hydroxide aqueous solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with distilled water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe product was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-6be89935bf2f49e196c5ae5385c2be5d
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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