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

HRID 2352514Notes

Reaction equation

HRID 2352514 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18](Cl)[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]([OH:26])[CH2:22][CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN(C)C=O>[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]([O:26][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)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 62761-PentanolHCID 24758Sodium hydrideHCID 639541HCID 639541, compound

Product 1

HCID 1295602-(4-Allyl-1-piperazinyl)-4-pentyloxyquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-(4-allyl-l-piperazinyl)-4-chloroquinazoline (3.0 g) obtained in Example 2 was suspended in 20 ml of N,N-dimethylformamide, and under ice cooling, 1 g of 1-pentanol and 0.5 g of sodium hydride (oily, 60 %) were added. The mixture was then stirred at room temperature for 4 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography [eluted with chloroform/methanol (30:1, v/v)] to give 2-(4-allyl-l-piperazinyl)-4-pentyloxyquinazoline as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. washeluted with chloroform/methanol (30:1

Sources & evidence

ORD record
ord-e1c781d4ba2942dc85a74bedb9d723a1
Source dataset
uspto-grants-1989_10
Patent number
US04877790

Reaction notes

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