Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1992-02-25
1993-08-31
Bond, Robert T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540322, 540586, 540594, 514213, C07D22316, A61K 3155
Patent
active
052410650
ABSTRACT:
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 R.sup.4 --X, wherein R.sup.4 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 R.sup.4 is 1-(1-cycloalkenyl) are novel.
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Berger Joel G.
Chang Wei K.
Kozlowski Joseph A.
Zhou Guowei
Blasdale John H. C.
Bond Robert T.
Kanstad Steinar V.
Mazer Edward H.
Schering Corporation
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