The preparation of <sup>15</sup>N‐phenoxybenzamine

Two complementary radiosynthetic routes to the potent PNMT inhibitor 7,8-dichloro-1 ,2,3,4-tetrahydroisoquinol i ne-l -l 4C(1) from 2,3-dichl orobenzal dehydeformyl-C(Q) are described. In the Pomeranz-Fritsch sequence isoquinoline 6 was prepared from Schiff's base 2.furnished 1 in 28% radiochemical yield from 4. sequence, 4 was converted via amino alcohol 7 to chloro amine 6. the latter with aluminum chloride/ammonium chloride (fusion, 190 "C) yielded labeled Jin 31% radiochemical yield from 2. 14 -Catalytic hydrogenation of fi (H2/Pt02) In the aluminum chloride fusion Treatment of m. i s 7.8-dichloro-l,2,3,4-tetrahydroisoquinol ine hydrochloride (1. S K f F 64139-A).(4) studies, we explored two complementary synthetic approaches both of which posi-One of the most potent of these agents. J I J In order to prepare carbon-14 tagged material for metabolite tioncd the carbon label in the 1-posltion of the tetrahydroisoquinoline. (5) The cmcn intermediate for the herein described methods was 2,3-dichlorobenzal-dehy~!e-formyl-'~C, readfly prepared from K CN. 14 RESULTSThe classical approach i s illustrated in SCHEHE 1. This method, which utilized the Pmeranz-Fritsch reaction(6a) for cyclization, produced 1 in 26-28 radiochemical yield from aldehyde 2. Commercial 2,3-dichloroiodobenzene SCHEME 1 CI CI DIBAL/

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The preparation and characterization of (±)‐[phenoxy‐³H(N)] phenoxybenzamine hydrochloride at high specific activity

Filer

Fazio

Morrison

et al. 1987

Labelled Comp Radiopharmac

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+)-Phenoxybenzamine is a ligand capable of irreversibly alkylating the alpha-1 adrenergic receptor. Previous attempts to radiolabel it have achieved only low specific activities which impeded their use in neurochemical investigations. (+)-[Phenoxy-JH(N)]Phenoxybenzamine.HC1 (1) has been prepared in our laboratory by the catalytic reductive aryl debrominatTon of an appropriate brominated precursor with tritium gas. 3H NMR showed exclusive radiolabeling on the phenoxy ring and the radioligand had a specific activity o f 32.4 Ci/mnol.

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The preparation of ¹⁵N‐phenoxybenzamine

Abstract: Phenoqbenzwnine ethylmine hydrochloride] has been labelled with Nitrogen-15 by a direct synthesis from "N-oniwn chloride. enrichment was 92.8%.The isotopic

Cited by 3 publications

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Two syntheses of 7,8‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐1‐¹⁴C

The preparation and characterization of (±)‐[phenoxy‐³H(N)] phenoxybenzamine hydrochloride at high specific activity

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The preparation of 15N‐phenoxybenzamine

Abstract: Phenoqbenzwnine ethylmine hydrochloride] has been labelled with Nitrogen-15 by a direct synthesis from "N-oniwn chloride. enrichment was 92.8%.The isotopic

Cited by 3 publications

References 3 publications

Synthesis of 1-chloro-1-[15N]nitrosocyclohexane, an electrophilic aminating reagent

Synthesis of 1-chloro-1-[15N]nitrosocyclohexane, an electrophilic aminating reagent

Two syntheses of 7,8‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐1‐14C

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The preparation of ¹⁵N‐phenoxybenzamine

Two syntheses of 7,8‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐1‐¹⁴C

The preparation and characterization of (±)‐[phenoxy‐³H(N)] phenoxybenzamine hydrochloride at high specific activity