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Synthesis of 1‐amino‐2‐β‐(3‐ [2,6‐ 14 C] piperidinome thylphenoxy) propylamino ‐1‐cyclobutene‐3,4‐dione hydrochloride
Author(s) -
Swigor J. E.,
Algieri A. A.,
Standridge R. T.,
Pittman K. A.
Publication year - 1985
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.2580220602
Subject(s) - chemistry , cyclobutene , hydrochloride , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry)
The synthesis of the title compound (6) is described. The condensation of 3‐aminopropanol with phthalic anhydride and subsequent treatment with phosphorous tribromide produced N‐[3‐bromopropyl] phthalimide. Acylation with 3‐hydroxybenzaldehyde, reduction with hydrogen over Raney nickel and subsequent treatment with thionyl chloride gave N‐[ 3‐(3‐chloromethylphenoxy) propyl ] phthalimide (2). Treatment with [2, 6 ‐ 14 C] piperidine introduced the radiolabel (3). Deprotection of the amino group with hydrazine and treatment with 3‐methoxy‐4‐amino‐3‐cyclobutene‐1,2‐dione produced 1‐amino‐2‐ [3‐(3‐[ 2,6‐ 14 C] piperidinome thylphenoxy) propylamino ]‐1‐cyclobutene‐3, 4‐dione (5). Treatment with hydrochloric acid yielded the title compound (6) in an overall chemical yield of 22%.