Phenethylamine → HCID 86617191, compound

HRID 1993486Notes

Reaction equation

HRID 1993486 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:20])([CH3:19])[O:4][C:5]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([N+:16]([O-:18])=[O:17])=[CH:8][C:6]=12.Cl([O-])(=O)(=O)=O.[Li+].[C:27]1([CH2:33][CH2:34][NH2:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:15][O:14][CH2:13][O:12][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[CH:8][C:6]2[C@@H:7]([NH:35][CH2:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:2]([OH:1])[C:3]([CH3:20])([CH3:19])[O:4][C:5]=2[CH:11]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 23665649Lithium perchlorateHCID 59134415HCID 59134415, compound

Product 1

HCID 86617191HCID 86617191, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,4-epoxy-7-methoxymethoxy-2,2-dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran (332 mg, 1.18 mmol) in dioxane (1.3 mL), lithium perchlorate (126 mg, 1.18 mmol) and 2-phenylethylamine (214 mg, 1.77 mmol) were added at room temperature, and the resulting mixture was stirred for 2 hours. Upon the completion of the reaction, saturated aqueous sodium hydrogencarbonate solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=3/1) and the aimed product was obtained (yield: 73%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-bd3f7641e0b5480f95d8833be93146fd
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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