Ammonia → HCID 12805659, compound

Participants

Reaction Steps

5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol (50.2 g) is partially dissolved in 350 ml of ether and added to 2 liters of liquid ammonia. Lithium ribbon (4.73 g) is then added portionwise over a period of 15 minutes. After stirring for 20 minutes, absolute alcohol is added dropwise until the color is discharged (about 90 ml added over a period of 1 hour). More ether is added and the ammonia is boiled off. While cooling in an ice bath the mixture is diluted slowly with 1 liter of water. The layers are separated and the aqueous layer is reextracted with ether. The combined organic layers are dried over potassium carbonate, filtered, and the solvent is removed in vacuo, leaving 47.0 g of an oil. NMR indicates this is about 50% of the desired diene (the bulk of remaining material being unreduced starting material).

Provenance & Evidence