4-Chloro-2-phenylquinazoline → 2-Phenyl-4-[4-(2-pyridinyl)-1-piperazinyl]quinazoline

HRID 354797Notes

Reaction equation

HRID 354797 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.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(O)(C)C>[C:1]1([C:7]2[N:16]=[C:15]([N:27]3[CH2:28][CH2:29][N:24]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)[CH2:25][CH2:26]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

4

Reactant 2

HCID 809774-Chloro-2-phenylquinazolineHCID 944591-(2-Pyridyl)piperazine

Product 1

HCID 102703292-Phenyl-4-[4-(2-pyridinyl)-1-piperazinyl]quinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture containing 9.6 g (0.04 mole) of 2-phenyl-4-chloroquinazoline, 6.4 g. (0.04 mole) of 1-(2-pyridyl) piperazine and 250 ml of isopropanol was refluxed for 4 hrs. The resulting reaction mixture was filtered after cooling to room temperature. The crystalline solid was dissolved in 400 ml of 3 N hydrochloric acid and the aqueous acidic liquid was washed with ether. The aqueous layer was adjusted to pH=7.5 which precipitated crystalline solid. This acidification and basification were repeated once. Yield of product was 6.8 g, m.p. 164°-166° C. (air dried).

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. dissolutionThe crystalline solid was dissolved in 400 ml of 3 N hydrochloric acid
  4. washthe aqueous acidic liquid was washed with ether
  5. customprecipitated crystalline solid
  6. custom6.8 g, m.p. 164°-166° C. (air dried)

Sources & evidence

ORD record
ord-413d1d78ceff433fb65a7d6ff6b37fbd
Source dataset
uspto-grants-1983_03
Patent number
US04377582

Reaction notes

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