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

HRID 1659956Notes

Reaction equation

HRID 1659956 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 3N 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 6.9 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 3N hydrochloric acid
  4. washthe aqueous acidic liquid was washed with ether
  5. customprecipitated crystalline solid
  6. custom6.9 g, m.p. 164°-166° C. (air dried)

Sources & evidence

ORD record
ord-739ec96bbf364c469165594461fbb27b
Source dataset
uspto-grants-1981_12
Patent number
US04306065

Reaction notes

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