Phenethylamine → HCID 49801658, compound

HRID 2425347Notes

Reaction equation

HRID 2425347 reaction equation
C([O:4][CH2:5][C:6]1[CH:15]=[C:14]([CH3:16])[C:13]2[CH:12]=[C:11]3[O:17][C:18]([CH3:23])([CH3:22])[C@@H:19]4[O:21][C@@H:20]4[C:10]3=[CH:9][C:8]=2[N:7]=1)(=O)C.Cl([O-])(=O)(=O)=O.[Li+].[C:30]1([CH2:36][CH2:37][NH2:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[OH:4][CH2:5][C:6]1[CH:15]=[C:14]([CH3:16])[C:13]2[CH:12]=[C:11]3[O:17][C:18]([CH3:22])([CH3:23])[C@H:19]([OH:21])[C@@H:20]([NH:38][CH2:37][CH2:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:10]3=[CH:9][C:8]=2[N:7]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 516892Sodium BicarbonateHCID 23665649Lithium perchlorateHCID 25197111HCID 25197111, compound

Product 1

HCID 49801658HCID 49801658, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (3R*,4R*)-(3,4-epoxy-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinolin-7-yl)-methyl acetate (403 mg, 1.29 mmol) in 1,4-dioxane (1 mL), lithium perchlorate (137 mg, 1.29 mmol) and phenylethylamine (0.195 mL, 1.55 mmol) were added at room temperature and the resulting mixture was stirred at 70° C. for 1.5 hour. Upon the completion of the reaction, sodium hydrogencarbonate aqueous solution was added to the reaction solution, and it was extracted with ethyl acetate. The resulting organic phase was washed with sodium hydrogencarbonate aqueous solution and then with sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by medium pressure column chromatography (hexane/ethyl acetate=1/1) and the aimed product was obtained (yield: 32%).

Workup

  1. additionwas added to the reaction solution, and it
  2. extractionwas extracted with ethyl acetate
  3. washThe resulting organic phase was washed with sodium hydrogencarbonate aqueous solution
  4. dry with materialwith sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by medium pressure column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e7b39f94619f474dad0fcdc1c5a8bdc3
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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