N'-methyl-N'-phenylbutane-1,4-diamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(4-Aminobutyl)-N-methylaniline (7.2 g) was dissolved in dichloromethane (70 ml) and maleic anhydride (4 g) was added thereto. The mixture was stirred at room temperature for 2 hours. The solvent was distilled off and then acetic anhydride (10 ml) was added. The resulting mixture was stirred at 100° C. for 5 hours. After concentration, an aqueous sodium bicarbonate was added to the residue to neutralize it. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with hexane/ethyl acetate (2:1) to obtain the desired compound (2.0 g) as yellow needles. The solvent was distilled off acetic anhydride (10 ml) was added The resulting mixture was stirred at 100° C. for 5 hours After concentration an aqueous sodium bicarbonate was added to the residue The mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure eluted with hexane/ethyl acetate (2:1)

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

Procedure: Lithium aluminium hydride (2 g) was added to dry ether (50 ml) in a stream of nitrogen, and a solution of N-(3-cyanopropyl)-N-methylaniline (9 g) in dry ether (10 ml) was added dropwise. The mixture was stirred for 1 hour and then heated under reflux for 2 hours. After decomposition of the excess reducing agent with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the desired compound (9.8 g) as colorless oil. heated under reflux for 2 hours the organic layer was washed with water dried over anhydrous sodium sulfate concentrated

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

Procedure: Lithium aluminium hydride (2 g) was added to dry ether (50 ml) in a stream of nitrogen, and a solution of N-(3-cyanopropyl)-N-methylaniline (9 g) in dry ether (10 ml) was added dropwise. The mixture was stirred for 1 hour and then heated under reflux for 2 hours. After decomposition of the excess reducing agent with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the desired compound (9.8 g) as colorless oil. heated under reflux for 2 hours the organic layer was washed with water dried over anhydrous sodium sulfate concentrated

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

Procedure: N-(4-Aminobutyl)-N-methylaniline (7.2 g) was dissolved in dichloromethane (70 ml) and maleic anhydride (4 g) was added thereto. The mixture was stirred at room temperature for 2 hours. The solvent was distilled off and then acetic anhydride (10 ml) was added. The resulting mixture was stirred at 100° C. for 5 hours. After concentration, an aqueous sodium bicarbonate was added to the residue to neutralize it. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with hexane/ethyl acetate (2:1) to obtain the desired compound (2.0 g) as yellow needles. The solvent was distilled off acetic anhydride (10 ml) was added The resulting mixture was stirred at 100° C. for 5 hours After concentration an aqueous sodium bicarbonate was added to the residue The mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure eluted with hexane/ethyl acetate (2:1)

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

Procedure: Lithium aluminium hydride (2 g) was added to dry ether (50 ml) in a stream of nitrogen, and a solution of N-(3-cyanopropyl)-N-methylaniline (9 g) in dry ether (10 ml) was added dropwise. The mixture was stirred for 1 hour and then heated under reflux for 2 hours. After decomposition of the excess reducing agent with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain the desired compound (9.8 g) as colorless oil. heated under reflux for 2 hours the organic layer was washed with water dried over anhydrous sodium sulfate concentrated