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Synthesis of N‐[4‐(2‐dimethylaminoethoxy) benzyl‐α‐ 14 C]‐3,4,5‐trimethoxybenzamide hydrochloride and N‐[4‐(2‐ methylaminoethoxy)benzyl‐α‐ 14 C]‐3, 4‐diethoxybenzamide hydrochloride
Author(s) -
Wineholt R. L.,
Johnson J. D.,
Heck P. J.,
Kaegi H. H.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060108
Subject(s) - hydrochloride , yield (engineering) , chemistry , alkoxy group , medicinal chemistry , organic chemistry , materials science , alkyl , metallurgy
The anti‐emetic compounds N‐[4‐(2‐dimethylaminoethoxy)benzyl‐α‐ 14 C]‐3,4,5‐trimethoxybenzamide hydrochloride (10) and N‐[4‐(2‐methylaminoethoxy)benzyl‐α‐ 14 C]‐3,4‐diethoxybenzamide hydrochloride (11) were prepared. The synthesis of 10 in four steps provided the purified material in 29 % yield from carbon dioxide. The same series of reactions was used to prepare N‐[4‐(2‐benzylmethylamino‐ethoxy)benzyl‐α‐ 14 C]‐3,4‐diethoxybenzamide (9), which after an additional debenzylation step furnished 11 in 56 % yield based on carbon dioxide.