Optically active 1-(fluoro-, trifluoromethyl- or...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S304000

Reexamination Certificate

active

07368609

ABSTRACT:
An optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative represented by the formula 4 is produced by a process including (a) reacting an optically active secondary amine, represented by the formula 1, with an alkylation agent R2—X, in the presence of a base, thereby converting the secondary amine into an optically active tertiary amine represented by the formula 3; and (b) subjecting the tertiary amine to a hydrogenolysis, thereby producing the N-monoalkyl derivative,wherein R represents a fluorine atom, trifluoromethyl group or trifluoromethoxy group, n represents an integer of from 1 to 5, each of R1and R2independently represents an alkyl group having a carbon atom number of from 1 to 6, Me represents a methyl group, Ar represents a phenyl group or 1- or 2-naphthyl group, * represents a chiral carbon, and X represents a leaving group.

REFERENCES:
patent: 2002/0103400 (2002-08-01), Ishii et al.
patent: 2003/0028021 (2003-02-01), Alvaro et al.
patent: 2004/0210817 (2004-10-01), Kapoor et al.
patent: WO 01/25219 (2001-04-01), None
patent: WO 02/32867 (2002-04-01), None
G.H. Posner et al., “ Methyl andn-Alkyl Ketones form Carboxylic Acid Chlorides and Organocopper Reagents”Tetrahedron Letters, No. 53, (1970) pp. 4647-4650, Great Britain.
Chemical Journal of Chinese Universities, Feb. 9, 1988, vol. 9, No. 2, pp. 134-139.
A. Gilbert, et al., “Excited State Substitution and Addition Reactions of Aryl Fluorides with Aliphatic Amines,” Department of Chemistry, University of Reading, Jul. 1980, pp. 1393-1399.
Japanese Office Action dated Jun. 16, 2006 and an English translation thereof (Eight (8) pages).
Correspondence dated Jul. 28, 2006 (Two (2) pages).

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