| Abstract: | The synthesis of 7-hydroxy, 8-hydroxy and 7,8-dihydroxy prochlorperazines (3a) and per-phenazines (3b) is reported. The parent ehlorophenothiazines were prepared analogously to previously reported chlorpromazine (3e) metabolite syntheses. The prochlorperazine side chain was introduced in one step using 1-(3-chloropropyl)-4-methylpiperazine and the perphenazine side chain in two steps, first reaction with 1-bromo-3-chloropropane followed by reaction with 1-piperazineethanol. The methoxymethyleneoxy O-proteetive groups were removed under mild conditions using methanolic hydrogen chloride. The preparations of 7-hydroxydesmethylprochlorperazine and 7-hydroxychlorpromazine quaternary methyl iodide are also reported. |
