Phthalimide → 2H-Isoindole-2-acetamide, 1,3-dihydro-1,3-dioxo-N-(2-phenylethyl)-

HRID 406928

Reaction equation

Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>>[C:14]1(=[O:24])[N:18]([CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4])[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12

Participants

Reactant 2

HCID 6809Phthalimide

HCID 949212-Chloro-N-phenethyl-acetamide

Product 1

HCID 6818082H-Isoindole-2-acetamide, 1,3-dihydro-1,3-dioxo-N-(2-phenylethyl)-

Procedure

KR2002076486 describes a process for preparation of praziquantel by reacting phenylethylamine with chloroacetyl chloride to obtain 2-chloro-N-phenethylacetamide. The compound 2-chloro-N-phenethylacetamide is then reacted with pthalimide to give 2-pthalimido-N-phenethylacetamide, which is then treated with hydrazine monohydrate to give 2-amino-N-phenylethylacetamide. On further treatment with bromoacetal, 2-amino-N-phenylethylacetamide gives 2-[2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide. This compound on further cyclization and acylation using cyclohexanoylchloride forms praziquantel.

Sources & evidence

ORD record: ord-0f46d89dde9f491b9fe7d968abcfd332
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754215B2

Linked notes

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