4-(N-methylanilino)butan-1-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 38.2 g (0.1 mole) of 4-triflylbenzenediazonium hexafluorophosphate in a 50:50 mixture of glacial acetic acid and water at 0° C. is added 17.9 g (0.1 mole) of N-4-hydroxybutyl-N-methylaniline dropwise. The reaction mixture is stirred at 0° C. for 15 minutes, and 12.3 g (0.15 mole) of sodium acetate is added with stirring. The reaction is stirred at 0° C. for 30 minutes and then warmed to room temperature and stirred for 16 hours. Compound C is collected by filtration and purified by recrystallization from ethanol. with stirring The reaction is stirred at 0° C. for 30 minutes warmed to room temperature stirred for 16 hours Compound C is collected by filtration purified by recrystallization from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the aqueous solution is extracted with methylene chloride The solvent is removed in vacuo the residual product is dissolved in a small amount of methylene chloride After removal of the silica gel the solution is filtered through cotton evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the aqueous solution is extracted with methylene chloride The solvent is removed in vacuo the residual product is dissolved in a small amount of methylene chloride After removal of the silica gel the solution is filtered through cotton evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the aqueous solution is extracted with methylene chloride The solvent is removed in vacuo the residual product is dissolved in a small amount of methylene chloride After removal of the silica gel the solution is filtered through cotton evaporated