1-Iodopentane → 2-(4-Allyl-1-piperazinyl)-4-pentyloxyquinazoline

HRID 2352512Notes

Reaction equation

HRID 2352512 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[NH:19][C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH2:21](I)[CH2:22][CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN(C)C=O>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 24758Sodium hydrideHCID 135804944HCID 135804944, compound

Product 1

HCID 1295602-(4-Allyl-1-piperazinyl)-4-pentyloxyquinazolineYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide was suspended 3.6 g of 2-(4-allyl-l-piperazinyl)-4(3H)-quinazolinone obtained in Example 1. With stirring under ice cooling, 3.6 g of pentyl iodide and 0.95 g of sodium hydride (oily, 60 %) were added to the suspension. The mixture was then stirred at 60° C. for 2.5 hours. Ice water (100 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography [eluted with chloroform/methanol (30:1, v/v)] to give 4.0 g of 2-(4-allyl-l-piperazinyl)-4-pentyloxyquinazoline as a pale yellow oil.

Workup

  1. stirringThe mixture was then stirred at 60° C. for 2.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with chloroform/methanol (30:1

Sources & evidence

ORD record
ord-f7fc8bcae9ad4257869ac4fa8309993c
Source dataset
uspto-grants-1989_10
Patent number
US04877790

Reaction notes

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