N,N,N',N'-Tetramethylethylenediamine → HCID 14677709, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromopyridine (37.9 g, 0.24 mol) in anhydrous ether (475 mL) at -75° C. under a nitrogen atmosphere was added n-butyllithium (160 mL of a 1.5 M hexane solution, 0.24 mol). Tetramethylethyenediamine (36.2 mL, 0.24 mol) was added and the solution was stirred at -75° C. for 1 hour. A solution of dibenzosuberone (50.l g, 0.24 mol) in anhydrous ether (250 mL) was added dropwise, the reaction mixture was stirred at -75° C. for 40 minutes, warmed to ambient temperature and stirred at that temperature for 1.5 hours. Water (650 mL) was added dropwise. The solid which crystallized was isolated by filtration to give 43.54 g of 10,11-dihydro-5-(4-pyridinyl)-5H-dibenzo[a,d]cyclohepten-5-ol, mp 174-177° C. Recrystallization from ethyl acetate-hexane gave material of mp 183-185° C.

Provenance & Evidence