Sodium Hydroxide → 4-(1-Acetyl-4-piperidinyl)-2-aminoquinazoline

HRID 617177Notes

Reaction equation

HRID 617177 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:25])[C:19]3C=CC=CC=3)[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+]>C(O)C>[C:18]([N:15]1[CH2:16][CH2:17][CH:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:13][CH2:14]1)(=[O:25])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 154287732-Amino-4-(1-benzoyl-4-piperidinyl)quinazoline

Product 1

HCID 154287764-(1-Acetyl-4-piperidinyl)-2-aminoquinazolineYield 66.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-(1-benzoyl-4-piperidinyl)quinazoline (24 g, 0.072 mol) obtained in Example 8 (3), ethanol (250 ml) and 6N sodium hydroxide aqueous solution (250 ml) was refluxed for about 7 hours under a nitrogen atmosphere. Thereafter ethanol was removed from the reaction mixture in vacuo. The residue was extracted with dichloromethane. The organic layer was washed with saturated sodium chloride aqueous solution, and then dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from isopropyl alcohol to give 13.0 g of the titled compound.

Workup

  1. temperaturewas refluxed for about 7 hours under a nitrogen atmosphere
  2. customThereafter ethanol was removed from the reaction mixture in vacuo
  3. extractionThe residue was extracted with dichloromethane
  4. washThe organic layer was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5c90be30ff2f48d5968c44e2c79bb7f6
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Reaction notes

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