Sodium Hydroxide → 1-(2-Phenyl-4-quinazolinyl)-4-piperidinol

HRID 354792Notes

Reaction equation

HRID 354792 reaction equation
[C:1]1([C:7]2[N:16]=[C:15](Cl)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[OH-].[Na+]>C(O)C>[C:1]1([C:7]2[N:16]=[C:15]([N:22]3[CH2:23][CH2:24][CH:19]([OH:18])[CH2:20][CH2:21]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 79341Piperidin-4-olHCID 809774-Chloro-2-phenylquinazoline

Product 1

HCID 127960301-(2-Phenyl-4-quinazolinyl)-4-piperidinolYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 6 g (0.025 mole) of 2-phenyl-4-chloroquinazoline, 3.53 g (0.035 mole) of 4-hydroxypiperidine and 100 ml of 95% ethyl alcohol was refluxed for 3 hrs. One gram of sodium hydroxide (in one ml of water) was added and the mixture was refluxed for an additional 2 hr period. The mixture was filtered and the filtrate was added to 300 ml of water. The white crystalline precipitate was separated and recrystallized with methanol and water to give 3.2 g of the title compound, m.p. 165°-167° C.

Workup

  1. temperaturewas refluxed for 3 hrs
  2. temperaturethe mixture was refluxed for an additional 2 hr period
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was added to 300 ml of water
  5. customThe white crystalline precipitate was separated
  6. customrecrystallized with methanol and water

Sources & evidence

ORD record
ord-33d5a86c5c804106a51224b633006abc
Source dataset
uspto-grants-1983_03
Patent number
US04377582

Reaction notes

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