Sulfuric Acid → Praziquanamine

HRID 1045647

Reaction equation

HRID 1045647 reaction equation
Cl.CO[CH:4](OC)[CH2:5][NH:6][CH2:7][C:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9].S(=O)(=O)(O)O>>[CH2:5]1[CH:4]2[C:18]3[C:13]([CH2:12][CH2:11][N:10]2[C:8](=[O:9])[CH2:7][NH:6]1)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 462240062,2-Dimethoxy-N-(2-oxo-2-((2-phenylethyl)amino)ethyl)ethanaminium chloride

Product 1

HCID 6453168PraziquanamineYield 75%

Procedure

2-(2,2-Dimethoxy-ethylamino)-N-phenethyl-acetamide hydrochloride (8.77 g, 29.0 mmol) was added to the ice-cooled sulfuric acid (8.8 ml) and the mixture was stirred for 3.5 hours at room temperature. Ice-water was added to the solution after cooling by ice and the resulting solution was extracted with dichloromethane after adjusted to pH 12 with 20% aqueous sodium hydroxide. The organic layer was washed with brine and dried with magnesium sulfate, and then the solvents were removed under reduced pressure. Recrystallization of the residue with hexane-ethyl acetate afforded 1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one (4.38 g, 75%).

Workup

  1. temperatureafter cooling by ice
  2. extractionthe resulting solution was extracted with dichloromethane after adjusted to pH 12 with 20% aqueous sodium hydroxide
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvents were removed under reduced pressure
  6. customRecrystallization of the residue with hexane-ethyl acetate

Sources & evidence

ORD record
ord-6da99e62545a4a7c9789c357dc93c5b8
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Linked notes

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