C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 223/16 (2006.01) A61K 31/55 (2006.01) C07C 231/12 (2006.01) C07D 209/34 (2006.01) C07D 213/56 (2006.01) C07D 217/24 (2006.01) C07D 225/06 (2006.01) C07D 233/64 (2006.01) C07D 277/30 (2006.01) C07D 307/54 (2006.01) C07D 333/24 (2006.01) C07D 491/056 (2006.01)
Patent
CA 2130797
A novel process for the preparation of .alpha.-substituted arylacetamides wherein the substituent is an aromatic group or a 1-alkenyl or 1-cycloalkenyl group and wherein the nitrogen atom carries no hydrogen atoms comprises the reaction of an arylacetamide having one or two hydrogen atoms on the .alpha.-carbon atom, wherein the nitrogen atom carries no hydrogen atoms, with a strong base in an inert aprotic organic solvent, followed by reaction with a zerovalent transition metal catalyst and then with a compound of the formula R4-X, wherein R4 is selected from aromatic groups, 1- alkenyl groups and 1-cycloalkenyl groups and X is a particular leaving group, especially a triflate group. The .alpha.- substituted arylacetamides are useful as intermediates in the preparation (by reduction) of .alpha.-substituted arylethylamines, e.g., 1- substituted-2,3,4,5-tetrahydro-1H-3-benzazepines, having pharmacological activity. Certain benzazepines wherein the 1-substituent R4 is 1-(1-cycloalkenyl) are novel.
Berger Joel G.
Chang Wei K.
Kozlowski Joseph A.
Zhou Guowei
Ogilvy Renault Llp/s.e.n.c.r.l.,s.r.l.
Schering Corporation
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