Two general routes to 1,4-disubstituted-2,3,4,5-tetrahydro- 1H-3-benzazepines.
[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the second route utilizes the addition of a Grignard reagent to the oxazolidine derived from a substitued phenylacetaldehyde and alpha-(methylaminomethyl)benzyl alcohol. In all cases studied, the cis-1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepine was obtained as the major product.
Gerritz
S W
SW
Glaxo Wellcome, Inc., Five Moore Drive, P.O. Box 13398, Research Triangle Park, North Carolina 27709, USA. swg25518@glaxowellcome.com
Smith
J S
JS
Nanthakumar
S S
SS
Uehling
D E
DE
Cobb
J E
JE
D001552:Benzazepines / Q000138:chemical synthesis*; D003500:Cyclization; D018492:Dopamine Antagonists / Q000138:chemical synthesis*; D019204:GTP-Binding Proteins / Q000378:metabolism; D007202:Indicators and Reagents; D017447:Receptors, Dopamine D1 / Q000037:antagonists & inhibitors
D001552:Benzazepines; D018492:Dopamine Antagonists; D007202:Indicators and Reagents; D017447:Receptors, Dopamine D1; D019204:GTP-Binding Proteins