7-dimethylamino-9-phenyl-6,7-dihydro [5H] benzocycloheptene → 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene

Participants

Reaction Conditions

Reaction Steps

5 g of palladized carbon [10% Pd(OH)2 ] were added to a solution of 5 g of 7-dimethylamino-9-phenyl-6,7-dihydro [5H] benzocycloheptene in 250 ml of ethanol and the mixture was stirred under a hydrogen atmosphere at 20° C until absorption ceased. The mixture was filtered and the filtrate was evaporated to dryness. The residue was chromatographed over silica gel and elution with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture yielded 0.52 g of isomer A (equatorial 5-H) and 2.9 g of isomer B (axial 5-H) of 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Provenance & Evidence