[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH3:12][N:13]([CH3:16])[CH:14]=O.C(N(CC)CC)C.[O-][Si]([O-])=O.[Mg+2]>CO.C(Cl)(Cl)Cl.C1C=CC=CC=1>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[C:7](=[CH:12][N:13]([CH3:16])[CH3:14])[CH2:6]1)(=[O:3])[CH3:2]
A reaction mixture was prepared from 15.5 g. of 4-acetamidocyclohexanone [prepared by the procedure of Fraser and Swingle, Can. J. Chem., 48, 2065 (1970)], 80 g. of the dimethylacetal of dimethylformamide, 1.5 ml. of triethylamine and 500 ml. of benzene. The benzene was distilled therefrom over a 1.5 hour period until the volume was reduced to about 1/2 of the original volume. An additional 250 ml. of benzene were added. The reaction mixture was heated just below the boiling point of benzene for about 2 hours and was then distilled again until the volume was about one-half of that originally present (250 ml.) The above process was repeated once more except that the volume was reduced to one-third of the original volume (167 ml.). The reaction mixture was then cooled and filtered. The filter cake consisted of dl-4-acetamido-2-dimethylaminomethylenecyclohexanone formed in the above reaction; weight=6.45 g. Evaporation of the filtrate to dryness yielded a residue, chromatography of a chloroform solution of which over 200 g. of Florisil using chloroform containing increasing amounts of methanol (0-5%) as an eluant, yielded more dl-4-acetamido-2-dimethylaminomethylenecyclohexanone; M.P.=132°-133° C. (from benzene); yield=5.55 g.; total yield=12 g.
読み込み中…
