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

Participants

Reaction Conditions

Reaction Steps

12.4 ml of ethanol and then a solution of 12 g of 7-dimethylamino-5ξ-phenyl-5ξ-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene in 200 ml of tetrahydrofuran were added to 600 ml of condensed ammonia and then 2.46 of sodium were added at -40° C. The mixture was stirred at -40° C for 20 minutes and the ammonia and tetrahydrofuran were evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture to obtain 3.2 g of isomer A (equatorial 5-H) and 6.5 g of isomer B (axial 5-H) of 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Provenance & Evidence