(+-)-p-Methoxyamphetamine → HCID 20026878, compound

HRID 1380138Notes

Reaction equation

HRID 1380138 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:20](=[O:24])[CH:21](O)O)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH:34]([NH2:36])[CH3:35])=[CH:29][CH:28]=1>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:20](=[O:24])[CH:21]=[N:36][CH:34]([CH3:35])[CH2:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31721(+-)-p-MethoxyamphetamineHCID 137449065-(2,2-Dihydroxyacetyl)-8-(phenylmethoxy)-2(1H)-quinolinone

Product 1

HCID 20026878HCID 20026878, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10.84 g of 8-benzyloxy-5-(dihydroxyacetyl)carbostyril 1/3 hydrate and 5.66 g of N-(2-(p-methoxyphenyl)-1-methylethyl)amine are dissolved in 100 ml of dimethylsulfoxide, and the solution is stirred at room temperature for one hour. The mixture is extracted with chloroform, and the extract is washed with water and a saturated sodium chloride solution, successively. The chloroform solution is dried and concentrated under reduced pressure to remove solvent. The residue is crystallized with a mixture of ethyl acetate and n-hexane, and crystalline precipitates are collected by filtration. 13 g of 8-benzyloxy-5-{1-oxo-2-[N-(2-(p-methoxyphenyl)-1-methylethyl)imino]ethyl}carbostyril are obtained as yellow solid. Yield: 87.6%

Workup

  1. extractionThe mixture is extracted with chloroform
  2. washthe extract is washed with water
  3. dry with materialThe chloroform solution is dried
  4. concentrationconcentrated under reduced pressure
  5. customto remove solvent
  6. customThe residue is crystallized with a mixture of ethyl acetate and n-hexane
  7. customcrystalline precipitates
  8. filtrationare collected by filtration

Sources & evidence

ORD record
ord-5a575437baa240e4825feac829701ce8
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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