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The synthesis of 1‐[(1‐methylethyl) amino]‐3‐{[(4‐methyl‐thio)‐1‐naphthalenyl]OXY}‐2‐propanol hydrochloride‐naphthalene‐11 14 C: 4′‐methylthiopropranolol
Author(s) -
Gransden D. F.,
Roth G. A.,
Takahashi I. T.
Publication year - 1983
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.2580200905
Subject(s) - chemistry , naphthalene , hydrochloride , yield (engineering) , high performance liquid chromatography , liquid scintillation counting , free base , chromatography , propanol , thio , nuclear chemistry , methanol , medicinal chemistry , organic chemistry , materials science , salt (chemistry) , metallurgy
The antihypertensive drug, 1‐[(1‐methylethyl)amino]‐3‐{[(4‐methylthio)‐1‐naphthalenyl ]oxy} ‐2‐propanol hydrochloride has been labeled with carbon‐14 in the 1‐position of the naphthalene. A total of 18.76 mCi was prepared in five steps starting with 1‐naphthol‐1‐ 14 C. The overall yield for the synthesis was 33.6% following five recrystallizations of the free base. The radiochemical purity of the hydrochloride product was 98.0% by high pressure liquid chromatography (HPLC)/liquid scintillation counting (LSC). The specific activity of the product was found to be 11.68 ∓ 0.45 mCi/mmole. Structural confirmation was done by infrared spectroscopy.