Synthesis of 7-benzyl-7-aza-3-thiabicyclo[3.3.1]nonane hydroperchlorate-6,8,10-14C3

✍ Scribed by Stan A. Zisman; K. Darrell Berlin; Fereidon K. Alavi; Subbiah Sangiah; Cyril R. Clarke; Benjamin J. Scherlag

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: French
• Weight: 202 KB
• Volume: 27
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580270804

✦ Synopsis

A synthesis of 7-benzyl-7-aza-3-thiabicyclo[3.3. llnonane hydroperchlorate-6,8,10-14C3 (2) is described via a Mannich type of condensation. 4-Thianone 14C-labelled benzylamine (14cH2) and paraformaldehyde [(H2'4C=O)n] in a solution of acetic acid with a small amount of concentrated HC1 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.l]nonan-9-one-6,8,10-14C3 a. 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 confmed the structure which had a specific activity of 0.64 pCUmg.