N,N,N',N'-tetramethyl-1-phenylmethanediamine

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

Procedure: 10 g (56 mmole) of N,N,N′, N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77 (1955) 1114-1116) were dissolved in 100 ml ether and the solution was cooled to 0° C. in an ice-bath. 4.0 ml (56 mmole) acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt precipitated out and the temperature increased slightly. After 15 hours at RT, the mixture was decanted and the solid was washed three times with 100 ml ether each time, filtered over an inert gas frit under nitrogen and dried to constant weight under an oil-pump vacuum. 7.7 g benzylidenedimethylammonium chloride (80.9% of theoretical) were obtained in this manner. After the first drops, a white salt precipitated out the temperature increased slightly the mixture was decanted the solid was washed three times with 100 ml ether each time filtered over an inert gas frit under nitrogen dried to constant weight under an oil-pump vacuum

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

Procedure: 10 g (56 mmole) of N,N,N′,N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77 (1955) 1114-1116) were dissolved in 100 ml of ether and cooled to 0° C. in an ice bath. 4.0 ml (56 mmole) of acetyl chloride were added under nitrogen. After the first few drops a white salt precipitated out and the temperature rose slightly. After 15 hours at RT the liquid was decanted off and the solids were washed three times, each time with 100 ml of ether, filtered under nitrogen through a protective gas frit, and dried to constant weight in an oil pump vacuum. 7.7 g of benzylidene dimethyl ammonium chloride (80.9% of theory) were obtained in this way. After the first few drops a white salt precipitated out After 15 hours at RT the liquid was decanted off the solids were washed three times each time with 100 ml of ether, filtered under nitrogen through a protective gas frit dried to constant weight in an oil pump vacuum

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

Procedure: 10 g (56 mmol) of N,N,N′,N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77,1955, p. 1114–1116) were dissolved in 100 ml of diethyl ether and cooled to 0° C. in an ice-bath. 4.0 ml (56 mmol) of acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt was precipitated, the temperature rose slightly. After 15 hours at room temperature, the supernatant liquor was decanted off and the solid was washed three times with 100 ml of diethyl ether each time, filtered over a protective gas frit under nitrogen and dried under an oil-pump vacuum until a constant weight was reached. In that manner, 7.7 g of benzylidenedimethylammonium chloride (corresponding to 81% of the theoretically calculated yield) were obtained. After the first drops, a white salt was precipitated the supernatant liquor was decanted off the solid was washed three times with 100 ml of diethyl ether each time filtered over a protective gas frit under nitrogen dried under an oil-pump vacuum until a constant weight

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

Procedure: 10 g (56 mmole) of N,N,N′, N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77 (1955) 1114-1116) were dissolved in 100 ml ether and the solution was cooled to 0° C. in an ice-bath. 4.0 ml (56 mmole) acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt precipitated out and the temperature increased slightly. After 15 hours at RT, the mixture was decanted and the solid was washed three times with 100 ml ether each time, filtered over an inert gas frit under nitrogen and dried to constant weight under an oil-pump vacuum. 7.7 g benzylidenedimethylammonium chloride (80.9% of theoretical) were obtained in this manner. After the first drops, a white salt precipitated out the temperature increased slightly the mixture was decanted the solid was washed three times with 100 ml ether each time filtered over an inert gas frit under nitrogen dried to constant weight under an oil-pump vacuum

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

Procedure: 10 g (56 mmole) of N,N,N′, N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77 (1955) 1114-1116) were dissolved in 100 ml ether and the solution was cooled to 0° C. in an ice-bath. 4.0 ml (56 mmole) acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt precipitated out and the temperature increased slightly. After 15 hours at RT, the mixture was decanted and the solid was washed three times with 100 ml ether each time, filtered over an inert gas frit under nitrogen and dried to constant weight under an oil-pump vacuum. 7.7 g benzylidenedimethylammonium chloride (80.9% of theoretical) were obtained in this manner. After the first drops, a white salt precipitated out the temperature increased slightly the mixture was decanted the solid was washed three times with 100 ml ether each time filtered over an inert gas frit under nitrogen dried to constant weight under an oil-pump vacuum