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Synthesis of 7‐benzyl‐7‐aza‐3‐thiabicyclo[3.3.1]nonane hydroperchlorate‐ 6,8,10 ‐ 14 C 3
Author(s) -
Zisman Stan A.,
Darrell Berlin K.,
Alavi Fereidon K.,
Sangiah Subbiah,
Clarke Cyril R.,
Scherlag Benjamin J.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270804
Subject(s) - chemistry , nonane , benzylamine , acetic acid , nuclear chemistry , benzyl alcohol , aqueous solution , methylamine , sodium hydroxide , acetic anhydride , triethylene glycol , amine gas treating , organic chemistry , medicinal chemistry , catalysis
A synthesis of 7‐benzyl‐7‐aza‐3‐thiabicyclo[3.3.1]nonane hydroperchlorate‐ 6,8,10 ‐ 14 C 3 ( 2 ) is described via a Mannich type of condensation. 4‐Thianone ( 3 ) was treated with 14 C‐labelled benzylamine ( 14 CH 2 ) and paraformaldehyde [(H 2 14 C =O) n ] in a solution of acetic acid with a small amount of concentrated HCl added for a period of six hours at reflux under nitrogen. Workup with aqueous sodium hydroxide followed by treatment with a high vacuum technique provided 7‐benzyl‐7‐aza‐3‐thiabicyclo[3.3.1]nonan‐9‐one‐ 6,8,10 ‐ 14 C 3 ( 4 ). Reduction of 4 under Wolff‐Kishner conditions with hydrazine/KOH in triethylene glycol at the boiling point of o ‐xylene provided the corresponding crude amine after workup. Treatment with 60% perchloric acid (below 5°C) resulted in the formation of the title compound 2 which could be recrystallized (95% ethanol). The melting point and spectral data confirmed the structure which had a specific activity of 0.64 μCi/mg.