Selective hydrogenation of a C3-C5 alkyl alchol

Details Selective hydrogenation of a C3-C5 alkyl alchol Selective hydrogenation of a C3-C5 alkyl alchol

1999-07-22

2001-09-04

Lambkin, Deborah C. (Department: 1626)

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

Organic compounds

Nitriles

Reexamination Certificate

active

06284913

ABSTRACT:

1. Field of the Invention
This invention relates to novel salts of cyanobenzylamines (CBAs), and to processes which may be used to produce such salts.
2. Prior Art
The selective hydrogenation of 1,4-dicyanobenzene to form 4-cyanobenzylamine (4-CBA) is a well known reaction.
For example, UK Patent No. 814,631 and Japanese Patent Application No. 49085041 both describe the hydrogenation of 1,4-dicyanobenzene in the presence of a palladium or a platinum catalyst, ammonia and, in the latter case, an inorganic alkali.
The hydrogenation of 1,4-dicyanobenzene in the presence of a palladium catalyst using methanol as a solvent has also been described in U.S. Pat. No. 3,050,544 and
Catalytic Hydrogenation over Platinum Metals,
Rylander, P., Academic Press, N.Y. (1967) at page 218.
None of these prior art documents refer to the use of a C
3-5
alkyl alcohol as a solvent.
Furthermore, in all of the abovementioned prior art documents, 4-CBA is isolated in the form of a free base. None disclose or suggest the isolation of 4-CBA in the form of a salt following its formation.
Salts of CBAs are known in the art, including the hydrochloride salt of 4-CBA (see, for example, McKay et al, J. Am. Chem. Soc. (1959) 81, 4328, Short et al, J. Med. Chem. (1967) 10, 833 and Goldberg et al, J. Chem. Soc. (1947) 1369). However, no CBA has ever been isolated in the form an alkanesulphonate salt.


REFERENCES:
patent: 3050544 (1962-08-01), Pietrusza et al.
patent: 814631 (1959-06-01), None
patent: 1 226 187 (1971-03-01), None
patent: 49085041 (1974-08-01), None
STN International, CAPLUS Database, Chemical Abstracts Service, (Columbus, Ohio), No. 1998:498623; abstract of JP 10-204048 (Aug. 4, 1998).*
STN International, CAPLUS Database, Chemical Abstracts Service, (Columbus, Ohio), No. 1998:543045; abstract of WO 98/33766 (Aug. 6, 1998).*
Rylander, P., “Catalytic Hydrogenation over Platinum Metals,” Academic Press, New York (1967) at p. 218.
McKay et al, J. Am. Chem. Soc., vol. 81, p. 4328 (1959).
Short et al, J. Med. Chem., vol. 10, p. 833 (1967).
Goldberg et al, J. Chem. Soc., p. 1369 (1947)

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