Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1985-02-11
1986-02-04
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546 86, C07D47104
Patent
active
045687498
ABSTRACT:
A novel process for preparing various 2-substituted-5-aryl-1,2,3,4-tetrahydro-.gamma.-carboline derivatives is provided, which involves (1) condensing a corresponding 2-unsubstituted compound with formaldehyde and an appropriate acetylenic derivative in the presence of cuprous chloride or cuprous bromide, followed by (2) reduction of the corresponding unsaturated intermediate to yield the desired final product. The latter compounds are known to be useful as tranquilizing agents, with 2-[4-(p-fluorophenyl)-4-hydroxybutyl]-5-(p-fluorophenyl)-8-fluoro-1,2,3,4- tetrahydro-.gamma.-carboline representing a preferred final product. The aforesaid unsaturated intermediates are all novel compounds.
REFERENCES:
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Midland, J. Org. Chem. 40, pp. 2250-2252 (1975).
Fowler, J. Org. Chem. 42, pp. 2637-2639 (1977).
Komarov et al., Chem. Abs. 79; 4898c (1973).
Zakumbaeva et al., Chem. Abs. 80; 137524v (1974).
Rylander, "Catalytic Hydrogenation over Platinum Metals", Academic Press, New York (1967), pp. 3-5.
Blackwood Robert K.
Frost Albert E.
Knuth Charles J.
Pfizer Inc.
Rotman Alan L.
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