Dimethylformamide → HCID 12962160, compound

Participants

Reaction Steps

Sodium hydride (4.28 g; 0.18 mole) is added portionwise with cooling (5°-10° C.) under nitrogen to a solution of 11-cyano-6,11-dihydrodibenz[b,e]oxepin (16.0 g; 0.72 mole), of Example 1A, in dry DMF (320 ml) and stirred at ambient temperature for 11/2 hours. At this time, 2-dimethylaminopropyl chloride hydrochloride (15.92 g; 0.10 mole) is added portionwise while maintaining the temperature below 10° C. Upon completion of the addition, stirring is continued at 80° C. for 20 hours. The reaction mixture is cooled, poured into 2 liters of ice water and extracted with ether. The ether is back extracted with 2 N HCl and the acidic washes combined and made basic with potassium carbonate. After extraction with ether and drying (K2CO3) the ether is removed in vacuo to give a solid. Trituration with hexane and drying provides 7.0 g (32%) of a solid (m.p. 112°-114° C.) of 11-cyano-11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin.

Provenance & Evidence