Phenethylamine → HCID 67246646, compound

HRID 2425362Notes

Reaction equation

HRID 2425362 reaction equation
O1[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[CH:7]([NH:35][CH2:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:2][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 67246646HCID 67246646, 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-benzopyrane (332 mg, 1.18 mmol) in dioxane (1.3 mL), lithium perchlorate (126 mg, 1.18 mmol) and 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 sodium hydrogencarbonate aqueous 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-1e2bfd04e9ee42b0ad6827f8a0f4481a
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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