Preparation of antifibrinolytically active isomer of 4-aminometh

Details Preparation of antifibrinolytically active isomer of 4-aminometh Preparation of antifibrinolytically active isomer of 4-aminometh

1979-01-30

1979-11-13

Killos, Paul J.

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

Organic compounds

Carboxylic acids and salts thereof

C07C10104

Patent

active

RE0301493

ABSTRACT:
Disclosed and claimed is the preparation of the 4-aminomethyl-cyclohexane carboxylic acid isomer assaying at least about 90% antifibrinolytically active material from specific para-disubstituted cyclohexane starting material. For example, in 4-aminomethyl-cyclohexane methanol such as its isomer melting at 118.degree. C. in a series of steps its methanol group is converted to carboxyl. More specifically its amino group is blocked by reaction with benzoyl halide and the methanol group then oxidized to carboxyl, and the benzoyl group removed to yield the end product isomer.
1-4-dimethyl-cyclohexane dicarboxylate melting at 69.degree.-71.degree. C., another such cyclohexane starting material, is hydrolyzed to its mono-ester which with thionyl halide is converted to the halide of the half-ester, which latter reacted with ammonia gives the corresponding ester amide. The latter is heated with thionyl halide and converted to methyl 4-cyano-cyclohexane carboxylate which then is hydrolyzed to yield 4-cyano-cyclohexane carboxylic acid which catalytically reduced using a compatible reduction catalyst such as Raney nickel is converted to the 4-aminomethyl-cyclohexane carboxylic acid end product.

REFERENCES:
Liebeg's Annalen der Chemie, vol. 310, p. 194 (1900).
Deruent Abstract of Belgium Pat. 617,216, Feb. 1, 1963.
Notler: Chemistry of Organic Compounds, 2nd ed.

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