N'-[(4-chlorophenyl)methyl]ethane-1,2-diamine

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

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

Procedure: The amine produced in Procedure 90, 14.5 g. (0.079 mole) was dissolved in 50 ml. of methanol and treated with a solution 9.1 g. (0.086 mole) of cyanogen bromide in 30 ml. of methanol in dropwise fashion. The warm solution was cooled to room temperature which resulted in the formation of a precipitate. The mixture was kept with stirring for 1/2 hr. and then a portion of the solvent was removed by distillation in vacuo. The solid product which separated was collected on a filter, washed with Et2O, and air dried, yield 16 g., m.p. 270°-272°. (0.079 mole) was dissolved in 50 ml resulted in the formation of a precipitate and then a portion of the solvent was removed by distillation in vacuo The solid product which separated was collected on a filter washed with Et2O, and air dried

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

Procedure: p-Chlorobenzyl chloride, 32 g. (0.2 mole), was added dropwise to 60 g. (1.0 mole) of ethylenediamine heated at 80°. The solution was stirred at 80° overnight and then the excess amine was distilled in vacuo. The residue was triturated with i-PrOH to yield 32 g. of crude product. This material was dissolved in water, basified with dilute NaOH and the solution extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated in vacuo to an oil. The latter was distilled and the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g. of the desired product, the identity of which was confirmed by examination of the NMR spectrum. (0.2 mole), was added dropwise to 60 g the excess amine was distilled in vacuo The residue was triturated with i-PrOH to yield 32 g the solution extracted with CH2Cl2 The combined extracts were dried (K2CO3) concentrated in vacuo to an oil The latter was distilled the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g

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

Procedure: The amine produced in Procedure 90, 14.5 g. (0.079 mole) was dissolved in 50 ml. of methanol and treated with a solution 9.1 g. (0.086 mole) of cyanogen bromide in 30 ml. of methanol in dropwise fashion. The warm solution was cooled to room temperature which resulted in the formation of a precipitate. The mixture was kept with stirring for 1/2 hr. and then a portion of the solvent was removed by distillation in vacuo. The solid product which separated was collected on a filter, washed with Et2O, and air dried, yield 16 g., m.p. 270°-272°. (0.079 mole) was dissolved in 50 ml resulted in the formation of a precipitate and then a portion of the solvent was removed by distillation in vacuo The solid product which separated was collected on a filter washed with Et2O, and air dried

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

Procedure: p-Chlorobenzyl chloride, 32 g. (0.2 mole), was added dropwise to 60 g. (1.0 mole) of ethylenediamine heated at 80°. The solution was stirred at 80° overnight and then the excess amine was distilled in vacuo. The residue was triturated with i-PrOH to yield 32 g. of crude product. This material was dissolved in water, basified with dilute NaOH and the solution extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated in vacuo to an oil. The latter was distilled and the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g. of the desired product, the identity of which was confirmed by examination of the NMR spectrum. (0.2 mole), was added dropwise to 60 g the excess amine was distilled in vacuo The residue was triturated with i-PrOH to yield 32 g the solution extracted with CH2Cl2 The combined extracts were dried (K2CO3) concentrated in vacuo to an oil The latter was distilled the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g

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

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

Procedure: The amine produced in Procedure 90, 14.5 g. (0.079 mole) was dissolved in 50 ml. of methanol and treated with a solution 9.1 g. (0.086 mole) of cyanogen bromide in 30 ml. of methanol in dropwise fashion. The warm solution was cooled to room temperature which resulted in the formation of a precipitate. The mixture was kept with stirring for 1/2 hr. and then a portion of the solvent was removed by distillation in vacuo. The solid product which separated was collected on a filter, washed with Et2O, and air dried, yield 16 g., m.p. 270°-272°. (0.079 mole) was dissolved in 50 ml resulted in the formation of a precipitate and then a portion of the solvent was removed by distillation in vacuo The solid product which separated was collected on a filter washed with Et2O, and air dried

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

Procedure: p-Chlorobenzyl chloride, 32 g. (0.2 mole), was added dropwise to 60 g. (1.0 mole) of ethylenediamine heated at 80°. The solution was stirred at 80° overnight and then the excess amine was distilled in vacuo. The residue was triturated with i-PrOH to yield 32 g. of crude product. This material was dissolved in water, basified with dilute NaOH and the solution extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated in vacuo to an oil. The latter was distilled and the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g. of the desired product, the identity of which was confirmed by examination of the NMR spectrum. (0.2 mole), was added dropwise to 60 g the excess amine was distilled in vacuo The residue was triturated with i-PrOH to yield 32 g the solution extracted with CH2Cl2 The combined extracts were dried (K2CO3) concentrated in vacuo to an oil The latter was distilled the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g

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

Procedure: The amine produced in Procedure 90, 14.5 g. (0.079 mole) was dissolved in 50 ml. of methanol and treated with a solution 9.1 g. (0.086 mole) of cyanogen bromide in 30 ml. of methanol in dropwise fashion. The warm solution was cooled to room temperature which resulted in the formation of a precipitate. The mixture was kept with stirring for 1/2 hr. and then a portion of the solvent was removed by distillation in vacuo. The solid product which separated was collected on a filter, washed with Et2O, and air dried, yield 16 g., m.p. 270°-272°. (0.079 mole) was dissolved in 50 ml resulted in the formation of a precipitate and then a portion of the solvent was removed by distillation in vacuo The solid product which separated was collected on a filter washed with Et2O, and air dried

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

Procedure: p-Chlorobenzyl chloride, 32 g. (0.2 mole), was added dropwise to 60 g. (1.0 mole) of ethylenediamine heated at 80°. The solution was stirred at 80° overnight and then the excess amine was distilled in vacuo. The residue was triturated with i-PrOH to yield 32 g. of crude product. This material was dissolved in water, basified with dilute NaOH and the solution extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated in vacuo to an oil. The latter was distilled and the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g. of the desired product, the identity of which was confirmed by examination of the NMR spectrum. (0.2 mole), was added dropwise to 60 g the excess amine was distilled in vacuo The residue was triturated with i-PrOH to yield 32 g the solution extracted with CH2Cl2 The combined extracts were dried (K2CO3) concentrated in vacuo to an oil The latter was distilled the material boiling at 93°-95°/0.06 mm Hg was collected to yield 14.5 g