Synthesis of cyclopentyl 2-thienyl ketone tiletamine and tiletam

Details Synthesis of cyclopentyl 2-thienyl ketone tiletamine and tiletam Synthesis of cyclopentyl 2-thienyl ketone tiletamine and tiletam

1999-02-16

1999-10-19

Lambkin, Deborah C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 70, C07D33322

Patent

active

059691590

ABSTRACT:
Solid, non-tin-containing catalysts can be used for the synthesis of cyclopentyl 2-thienyl ketone by the reaction of cyclopentanecarboxylic acid chloride and thiophene, while achieving new and unexpected yields. Aluminum trichloride is both cheaper than stannic chloride and it is easier to deal with as a waste stream. The successful use of graphite as a catalyst for the reaction of cyclopentanecarboxylic acid chloride and thiophene provides a mild and ecologically friendly method for carrying out the Friedel-Crafts reaction. A tiletamine-free base can be made from the cyclopentyl 2-thienyl ketone with a halide in the presence of a solvent for the cyclopentyl 2-thienyl ketone to form a halogenated cyclopentane 2-thienyl ketone; aminating the halogenated cyclopentane 2-thienyl ketone by reaction with an amine; and subjecting the reaction product to thermal rearrangement, in a suitable solvent, and at a sufficient temperature to form tiletamine free base. Each step for the formation of tiletamine free base can be accomplished using the same solvent, e.g., dichlorobenzene so that intermediates need not be isolated between reactions.

REFERENCES:
patent: 3342836 (1967-09-01), L'Italien
patent: 3522273 (1970-07-01), Parcell
patent: 4761486 (1988-08-01), Zeeh et al.
patent: 5034400 (1991-07-01), Olney
patent: 5597832 (1997-01-01), Michaelides et al.
patent: 5616580 (1997-04-01), Olney
patent: 5648087 (1997-07-01), Ovaert et al.
Clerici, F., et al., "N'-Arylsulfonylamidines: Part 2. A New Synthesis of Ketones from N-Tosylamidines and Organolithium Compounds", Synthesis Nov. 1987, pp. 1025-1027.
Jur'ew, Yu K., et al., ZH. Obshch-Khim 26 (1956), pp. 3341-3344.

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