Process for preparing carboline derivatives

Details Process for preparing carboline derivatives Process for preparing carboline derivatives

1981-12-17

1985-04-09

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

045103089

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:
patent: 4001263 (1974-01-01), Plattner et al.
Fowler, Journal of Organic Chemistry, vol. 42, No. 15, pp. 2637-2639, (1977).
Komarov et al., Chem. Abstracts, vol. 79, No. 1, 4898-c, Jul. 9, 1973.
Zakumbaeva et al., Chem. Abstracts, vol. 80, No. 24, 137, 524-v, Jun. 17, 1974.
M. M. Midland in the Journal of Organic Chemistry, vol. 40, No. 15, p. 2250, (1975).

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