[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[I-].[K+].C(=O)(O)[O-].[Na+]>CS(C)=O.O>[OH:14][CH2:13][CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
A stirred solution of 107.2 g (1 mole) of N-methylaniline, 153.0 g (1 mole) of 4-bromo-1-butanol, 166 g (1 mole) of potassium iodide, and 168 g (2 mole) of sodium bicarbonate in dimethylsulfoxide is heated at 90° C. until the reaction is complete as indicated by thin layer chromatography. After cooling to room temperature, the reaction mixture is poured into a four-fold excess of water, and the aqueous solution is extracted with methylene chloride. The solvent is removed in vacuo, and the residual product is dissolved in a small amount of methylene chloride and swirled with silica gel. After removal of the silica gel, the solution is filtered through cotton and evaporated to yield compound A.
Loading…
