Method for preparing opipramol

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

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540588, C07D22324, C07D40306

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active

055999298

ABSTRACT:
An improved method for preparing opipramol (I) is disclosed, wherein iminostilbene (II) is reacted with 1-bromo-3-chloropropane in the presence of a weak base selected from a hydrogen phosphate salt and an acetate salt and in the presence of a phase transfer agent to produce N-(3-halopropyl)iminostilbene (III), which is mixture of N-(3-chloropropyl)iminostilbene and N-(3-bromopropyl)iminostilbene, and then N-(3-halopropyl)iminostilbene is reacted with N-(2-hydroxyethyl)piperazine to form opipramol, as shown in the following equations, where X is chlorine or bromine. ##STR1##

REFERENCES:
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S. J. Schmolka et al., N-Dimethylaminopropylation in a Solid-Liquid Two Phase System: Synthesis of Chlorpromazine, its Analogs, and Related Compounds, Synthesis, No. 1, Stuttgart, Germany, Jan. 1984, pp. 29-31.
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E. D. Bergmann et al., Some Derivatives of 5H-Dibenz[b.f]Azepine, Tetrahedron, 1968, vol. 24, pp. 1289-1292. month of publication not provided.
L. J. Kricka et al., Reactions of Condensed N-Heteroaromatic Molecules. J. Chem. Soc., 1972, pp. 2292-2293 month of publication not provided.
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Hannig, E. Pharmazie34, 670-671 (1979). CA Abstract No. 93:26248.

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