Phenethylamine → 2-Chloro-N-phenethyl-acetamide

HRID 406927

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4]2C3CN(C(C4CCCCC4)=O)[CH2:13][C:14](=[O:15])[N:9]3[CH2:8][CH2:7][C:5]=2[CH:6]=1.C1(CCN)C=CC=CC=1.[Cl:33]CC(Cl)=O>>[Cl:33][CH2:13][C:14]([NH:9][CH2:8][CH2:7][C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][CH:6]=1)=[O:15]

Participants

Reactant 3

HCID 1001Phenethylamine

HCID 4891Praziquantel

HCID 6577Chloroacetyl chloride

Product 1

HCID 949212-Chloro-N-phenethyl-acetamide

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-31f5ab1927e74c42a4d5902d3e377ead
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754215B2

Linked notes

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