Phenethylamine → 2-Chloro-N-phenethyl-acetamide

HRID 406929Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13].C(=O)(O)[O-].[Na+]>>[Cl:10][CH2:11][C:12]([NH:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

Reactant 3

HCID 1001Phenethylamine

HCID 6577Chloroacetyl chloride

HCID 516892Sodium Bicarbonate

Product 1

HCID 949212-Chloro-N-phenethyl-acetamide

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-630e4e8c7c594a8ea67ad3b63a7af42f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754215B2

Reaction notes

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