N'-benzhydrylethane-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: A solution of 2.9 g of benzyl chloride in 25 ml of acetonitrile is added to 5.6 g of N-diphenylmethyl-ethylenediamine in 30 ml of boiling acetonitrile. The mixture is heated under reflux for 12 hours, concentrated and partitioned between diethyl ether and 10% sodium hydroxide solution. The organic phases are dried over sodium sulphate and concentrated by evaporation. The residue can be recrystallised from methanol or diisopropyl ether. N,N-dibenzyl-N'-diphenylmethyl-ethylenediamine having a melting point of 89°-91° C. is obtained. The mixture is heated under reflux for 12 hours concentrated partitioned between diethyl ether and 10% sodium hydroxide solution The organic phases are dried over sodium sulphate concentrated by evaporation The residue can be recrystallised from methanol or diisopropyl ether

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

Procedure: 11 g of N-diphenylmethyl-ethylenediamine, 10.1 g of triethylamine and 7.0 g of 1-phenylethyl chloride are dissolved, while stirring, in 85 ml of acetonitrile and heated under reflux for 30 hours. The solution is concentrated by evaporation under reduced pressure, 50 ml of 10% sodium hydroxide solution are added and the mixture is extracted thoroughly by shaking with diethyl ether. The ether extracts are combined, dried over sodium sulphate and concentrated by evaporation. N-diphenylmethyl-N'-(1-phenylethyl)-ethylenediamine is obtained in the form of a yellow oil which can be purified chromatographically over silica gel with methanol/ethyl acetate (1:1) as the eluant and, for characterisation, can be converted into the dihydrochloride, having a melting point of 160° C., as described in Example 4. heated under reflux for 30 hours The solution is concentrated by evaporation under reduced pressure, 50 ml of 10% sodium hydroxide solution are added the mixture is extracted thoroughly dried over sodium sulphate concentrated by evaporation

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

Procedure: A mixture of 90.15 g of ethylenediamine, 50.7 g of benzhydryl chloride and 300 ml of acetonitrile is heated under reflux for 24 hours. It is partitioned between 400 ml of diethyl ether and 175 ml of 10% sodium hydroxide solution, the ether phase is separated off, dried over magnesium sulphate, evaporated to dryness and distilled under reduced pressure. N-diphenylmethylethylenediamine is obtained, b.p.0.13 =116°-124° C., m.p. 23°-24° C. is heated under reflux for 24 hours It is partitioned between 400 ml of diethyl ether and 175 ml of 10% sodium hydroxide solution the ether phase is separated off dried over magnesium sulphate evaporated to dryness distilled under reduced pressure

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

Procedure: A solution of 9.2 g of α-chlorophenylacetic acid methyl ester, dissolved in 10 ml of acetonitrile, is added dropwise in the course of 10 minutes, while stirring, to a mixture of 11.3 g of N-diphenylmethyl-ethylenediamine, 5.05 g of triethylamine and 70 ml of acetonitrile. The mixture is then heated under reflux for 18 hours. It is then concentrated to dryness by evaporation under reduced pressure, triturated with 100 ml of 10% sodium hydroxide solution and extracted twice by shaking with 100 ml of diethyl ether each time. The ether phases are combined, washed three times with 30 ml of saturated sodium chloride solution each time, dried over magnesium sulphate and concentrated by evaporation. The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine. The ether phases are further treated as indicated above. Finally, drying is effected at approximately 0.15 mbar. N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine is obtained which is converted into the diacetate for characterisation. For that purpose, 14.8 g of base are dissolved in 15 ml of diethyl ether and 15 ml of hexane, and glacial acetic acid is added dropwise while stirring and cooling. The precipitate is filtered with suction, recrystallised from approximately 360 ml of diethyl ether and 90 ml of hexane and dried under reduced pressure (under 0.2 mbar). The N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine acetate melts at 78°-81° C. Pure N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine can be freed from this by treatment with 10% sodium hydroxide solution, extraction by shaking with diethyl ether, drying over magnesium sulphate and evaporating off the solvent. is added dropwise in the course of 10 minutes The mixture is then heated under reflux for 18 hours It is then concentrated to dryness by evaporation under reduced pressure triturated with 100 ml of 10% sodium hydroxide solution extracted twice washed three times with 30 ml of saturated sodium chloride solution each time dried over magnesium sulphate concentrated by evaporation The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine The ether phases are further treated Finally, drying

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

Procedure: A solution of 9.2 g of α-chlorophenylacetic acid methyl ester, dissolved in 10 ml of acetonitrile, is added dropwise in the course of 10 minutes, while stirring, to a mixture of 11.3 g of N-diphenylmethyl-ethylenediamine, 5.05 g of triethylamine and 70 ml of acetonitrile. The mixture is then heated under reflux for 18 hours. It is then concentrated to dryness by evaporation under reduced pressure, triturated with 100 ml of 10% sodium hydroxide solution and extracted twice by shaking with 100 ml of diethyl ether each time. The ether phases are combined, washed three times with 30 ml of saturated sodium chloride solution each time, dried over magnesium sulphate and concentrated by evaporation. The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine. The ether phases are further treated as indicated above. Finally, drying is effected at approximately 0.15 mbar. N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine is obtained which is converted into the diacetate for characterisation. For that purpose, 14.8 g of base are dissolved in 15 ml of diethyl ether and 15 ml of hexane, and glacial acetic acid is added dropwise while stirring and cooling. The precipitate is filtered with suction, recrystallised from approximately 360 ml of diethyl ether and 90 ml of hexane and dried under reduced pressure (under 0.2 mbar). The N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine acetate melts at 78°-81° C. Pure N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine can be freed from this by treatment with 10% sodium hydroxide solution, extraction by shaking with diethyl ether, drying over magnesium sulphate and evaporating off the solvent. is added dropwise in the course of 10 minutes The mixture is then heated under reflux for 18 hours It is then concentrated to dryness by evaporation under reduced pressure triturated with 100 ml of 10% sodium hydroxide solution extracted twice washed three times with 30 ml of saturated sodium chloride solution each time dried over magnesium sulphate concentrated by evaporation The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine The ether phases are further treated Finally, drying

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

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

Procedure: A solution of 2.9 g of benzyl chloride in 25 ml of acetonitrile is added to 5.6 g of N-diphenylmethyl-ethylenediamine in 30 ml of boiling acetonitrile. The mixture is heated under reflux for 12 hours, concentrated and partitioned between diethyl ether and 10% sodium hydroxide solution. The organic phases are dried over sodium sulphate and concentrated by evaporation. The residue can be recrystallised from methanol or diisopropyl ether. N,N-dibenzyl-N'-diphenylmethyl-ethylenediamine having a melting point of 89°-91° C. is obtained. The mixture is heated under reflux for 12 hours concentrated partitioned between diethyl ether and 10% sodium hydroxide solution The organic phases are dried over sodium sulphate concentrated by evaporation The residue can be recrystallised from methanol or diisopropyl ether

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

Procedure: 11 g of N-diphenylmethyl-ethylenediamine, 10.1 g of triethylamine and 7.0 g of 1-phenylethyl chloride are dissolved, while stirring, in 85 ml of acetonitrile and heated under reflux for 30 hours. The solution is concentrated by evaporation under reduced pressure, 50 ml of 10% sodium hydroxide solution are added and the mixture is extracted thoroughly by shaking with diethyl ether. The ether extracts are combined, dried over sodium sulphate and concentrated by evaporation. N-diphenylmethyl-N'-(1-phenylethyl)-ethylenediamine is obtained in the form of a yellow oil which can be purified chromatographically over silica gel with methanol/ethyl acetate (1:1) as the eluant and, for characterisation, can be converted into the dihydrochloride, having a melting point of 160° C., as described in Example 4. heated under reflux for 30 hours The solution is concentrated by evaporation under reduced pressure, 50 ml of 10% sodium hydroxide solution are added the mixture is extracted thoroughly dried over sodium sulphate concentrated by evaporation

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

Procedure: A mixture of 90.15 g of ethylenediamine, 50.7 g of benzhydryl chloride and 300 ml of acetonitrile is heated under reflux for 24 hours. It is partitioned between 400 ml of diethyl ether and 175 ml of 10% sodium hydroxide solution, the ether phase is separated off, dried over magnesium sulphate, evaporated to dryness and distilled under reduced pressure. N-diphenylmethylethylenediamine is obtained, b.p.0.13 =116°-124° C., m.p. 23°-24° C. is heated under reflux for 24 hours It is partitioned between 400 ml of diethyl ether and 175 ml of 10% sodium hydroxide solution the ether phase is separated off dried over magnesium sulphate evaporated to dryness distilled under reduced pressure

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

Procedure: A solution of 9.2 g of α-chlorophenylacetic acid methyl ester, dissolved in 10 ml of acetonitrile, is added dropwise in the course of 10 minutes, while stirring, to a mixture of 11.3 g of N-diphenylmethyl-ethylenediamine, 5.05 g of triethylamine and 70 ml of acetonitrile. The mixture is then heated under reflux for 18 hours. It is then concentrated to dryness by evaporation under reduced pressure, triturated with 100 ml of 10% sodium hydroxide solution and extracted twice by shaking with 100 ml of diethyl ether each time. The ether phases are combined, washed three times with 30 ml of saturated sodium chloride solution each time, dried over magnesium sulphate and concentrated by evaporation. The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine. The ether phases are further treated as indicated above. Finally, drying is effected at approximately 0.15 mbar. N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine is obtained which is converted into the diacetate for characterisation. For that purpose, 14.8 g of base are dissolved in 15 ml of diethyl ether and 15 ml of hexane, and glacial acetic acid is added dropwise while stirring and cooling. The precipitate is filtered with suction, recrystallised from approximately 360 ml of diethyl ether and 90 ml of hexane and dried under reduced pressure (under 0.2 mbar). The N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine acetate melts at 78°-81° C. Pure N-(α-methoxycarbonylbenzyl)-N'-diphenylmethyl-ethylenediamine can be freed from this by treatment with 10% sodium hydroxide solution, extraction by shaking with diethyl ether, drying over magnesium sulphate and evaporating off the solvent. is added dropwise in the course of 10 minutes The mixture is then heated under reflux for 18 hours It is then concentrated to dryness by evaporation under reduced pressure triturated with 100 ml of 10% sodium hydroxide solution extracted twice washed three times with 30 ml of saturated sodium chloride solution each time dried over magnesium sulphate concentrated by evaporation The residue obtained after concentration by evaporation is shaken with 10% (by weight) sodium hydroxide solution and diethyl ether in order to remove any excess triethylamine The ether phases are further treated Finally, drying

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