1-Phenylpiperazine → HCID 19079292, compound

HRID 964024Notes

Reaction equation

HRID 964024 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([CH2:11][CH2:12]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=[C:5]2[O:4][CH2:3]1.[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.[O:43]1CCOCC1>>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([CH2:11][CH2:12][N:33]3[CH2:34][CH2:35][N:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:31][CH2:32]3)[CH:10]=[C:5]2[O:4][C:3]1=[O:43]

Participants

5

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86752778HCID 86752778, compound

Product 1

HCID 19079292HCID 19079292, compound

Procedure

3-methyl-6-[2-(p-toluenesulfonyloxy)ethyl]oxazolo[4,5-b]pyridin-2(3-one of Preparation 15 (210 mg, 1.2 mmol) is dissolved in 1,4-dioxane (8 ml). N-phenyl-piperazine (0.10 ml, 1.38 mmol) and triethylamine (0.18 ml, 1.3 mmol) are added in succession to the reaction mixture. Stirring is maintained at room temperature for 24 hours. After the solvent has been evaporated off under reduced pressure, the residue is taken up in water. Extraction is carried out with dichloromethane and the organic phase is dried over magnesium sulfate and filtered, and then the solvent is evaporated off. The title product is purified by chromatography on silica gel (eluant: dichloromethane/methanol: 95/5). The yield obtained is 91%. ##STR66##

Workup

  1. customAfter the solvent has been evaporated off under reduced pressure
  2. extractionExtraction
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off
  6. customThe title product is purified by chromatography on silica gel (eluant: dichloromethane/methanol: 95/5)
  7. customThe yield obtained

Sources & evidence

ORD record
ord-d4d74c9b8f06469e89c62bebfe587543
Source dataset
uspto-grants-1998_06
Patent number
US05767128

Reaction notes

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