Reductive alkylation of saturated cyclic amines

Details Reductive alkylation of saturated cyclic amines Reductive alkylation of saturated cyclic amines

2007-04-03

2007-04-03

Wilson, James O. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

active

10726091

ABSTRACT:
Saturated cyclic amines (e.g., piperazines and piperidines) are reductively alkylated with an N-containing heteroaryl carbaldehyde using an alkylcarboxylic acid and a borohydride to obtain a product comprising an N-((N-containing heteroaryl)methyl)-substituted cyclic amine and one or more borane complexes thereof, after which the product is treated with a catalytic amount of a Pt or Pd catalyst in the presence of an alcohol to cleave the borane complex(es) and thereby afford the N-((N-containing heteroaryl)methyl)cyclic amine free of borane complex. Saturated cyclic amines are also reductively alkylated by adding an N-containing heteroaryl carbaldehyde and the amine to a tetrahydroborate salt-alkylcarboxylic acid-solvent admixture and aging the resulting reaction mixture to obtain an alkylated product substantially free of borane complex.

REFERENCES:
patent: 5413999 (1995-05-01), Vacca et al.
patent: 5508404 (1996-04-01), Askin et al.
patent: 5618937 (1997-04-01), Askin et al.
patent: 6642237 (2003-11-01), Tata et al.
patent: WO 01/38332 (2001-05-01), None
G.W. Gribble et al., “Sodium Borohydride in Carboxylic Acid Media. A Review of the Synthetic Utility of Acyloxyborohydrides”, 1985, vol. 17 (4-5), pp. 317-384, Organic Preparations and Procedures Int.
C.F. Nutaltis, “Reacations of Borohydride in Carboxylic Acid Media: a Summary”, 1989, vol. 66, pp. 673-675, J. Chemical Education.
A.E. Moormann, “Reductive Amination of Piperidines with Aldehydes Using Borane-Pyridine”, 1993, vol. 23, pp. 789-795, Synthetic Communications.
A.F. Abdel-Magid et al., “Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures”, 1996, vol. 61, pp. 3849-3862, J. Organic Chemistry.
M. Couturier et al., “Palladium and Raney Nickel Catalyzed Methanolic Cleaveage of Stable Borane-Amine Complexes”, 2001, vol. 3, pp. 465-467, Organic Letters.

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