8-Hydroxyquinoline → HCID 20079037, compound

HRID 1195704Notes

Reaction equation

HRID 1195704 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH3:18][C:19](C)([O-:21])[CH3:20].[K+].[OH-].[Na+].[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1>>[C:26]1([CH:30]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:11]=2)[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([OH:21])[CH2:20][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[C:6]4[C:11]=3[N:10]=[CH:9][CH:8]=[CH:7]4)[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=[CH:28][CH:27]=1

Participants

6

Reactant 5

HCID 19238-HydroxyquinolineHCID 4837PiperazineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 20079037HCID 20079037, compound

Procedure

In 5 ml of dried THF were dissolved 200 mg of 8-hydroxyquinoline and 319 mg of the piperazine compound prepared in Example 23-(b), and 120 mg of potassium t-butoxide was further added thereto. The liquid was then stirred at room temperature for 5 days, and 20 ml of a 1N aqueous sodium hydroxide solution was poured into the liquid, followed by extracting with 100 ml of methylene chloride. Afterward, the methylene chloride solution was washed with a dilute aqueous sodium hydroxide solution, and was then dried with an anhydrous Glauber's salt. After the solvent was distilled off, the residue was purified through a silica gel column chromatograph. On allowing an effluent solvent of chloroform:methanol=50:1 to flow therethrough, the desired product 8-[3-(4-diphenylmethylpiperazine-1-yl)-2-hydroxypropoxy]-quinoline was obtained in a powdery state in an amount of 45 mg.

Workup

  1. additionwas further added
  2. extractionby extracting with 100 ml of methylene chloride
  3. washAfterward, the methylene chloride solution was washed with a dilute aqueous sodium hydroxide solution
  4. dry with materialwas then dried with an anhydrous Glauber's salt
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified through a silica gel column chromatograph

Sources & evidence

ORD record
ord-12f86f2c0f16462e9bb9454fd8f8ff9c
Source dataset
uspto-grants-1992_05
Patent number
US05112817

Reaction notes

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