Sulfuric Acid → Praziquanamine

HRID 406931Notes

Reaction equation

HRID 406931 reaction equation
CO[CH:3]([O:18]C)[CH2:4][NH:5][CH2:6][C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.S(=O)(=O)(O)O>>[CH2:11]1[C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]2[CH2:6][NH:5][CH2:4][C:3](=[O:18])[N:9]2[CH2:10]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 109246802-((2,2-Dimethoxyethyl)amino)-N-(2-phenylethyl)acetamide

Product 1

HCID 6453168Praziquanamine

Procedure

Eur. J. Org. Chem. 2008, 895-913 describes a process comprising: a) reacting phenylethylamine with chloroacetyl chloride in presence of sodium bicarbonate to obtain 2-chloro-N-phenethylacetamide, b) treating 2-chloro-N-phenethylacetamide with aminoacetaldehyde dimethylacetal to give 2-[2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide, c) making hydrochloride salt of 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide, and d) cyclising using sulphuric acid to form praziquanamine (i.e.4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline).

Sources & evidence

ORD record
ord-707039dc536745fcbf8b56cd6ace7663
Source dataset
uspto-grants-2014_06
Patent number
US08754215B2

Reaction notes

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