N-(2-aminoethyl)-4-chlorobenzamide;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 6.2 ml (0.05 mol) of 4-chlorobenzoyl chloride in 150 ml of ether is added dropwise at -10° over a period of 0.5 hour to a solution of 10 ml (0.15 mol) of ethylenediamine in 150 ml of ether. The mixture is left to warm to room temperature, filtered and the white residue is rinsed twice with ether. After concentrating the ether solution, the residue is acidified with dilute hydrochloric acid and extracted several times with ethyl acetate in order to remove the neutral constituents. The aqueous phase is made alkaline with sodium hydroxide solution and extracted several times with chloroform. After evaporating the chloroform, converting the residue into the hydrochloride and recrystallization from ethanol/ether, there are obtained 1.8 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride which is identical with the product obtained in Example 1. The mixture is left filtered the white residue is rinsed twice with ether After concentrating the ether solution extracted several times with ethyl acetate in order to remove the neutral constituents extracted several times with chloroform After evaporating the chloroform into the hydrochloride and recrystallization from ethanol/ether, there

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 23 ml (0.17 mol) of triethylamine are added dropwise at 0° to a suspension of 23.5 g (0.15 mol) of 4-chlorobenzoic acid and 15 ml (0.16 mol) of ethyl chloroformate in 200 ml of chloroform. After completion of the addition (0.5 hour), the solution obtained is added dropwise at 0° to a solution of 50 ml (0.75 mol) of ethylenediamine in 100 ml of chloroform. After completion of the reaction, 115 ml of concentrated hydrochloric acid are added dropwise at 0°. The acidic mixture is filtered and the neutral constituents remaining are removed by extraction with chloroform. The aqueous phase is then made alkaline with sodium hydroxide solution and extracted several times with chloroform. The chloroform extracts are dried and concentrated. The residue is converted into the hydrochloride which is recrystallized from ethanol/ether. There are obtained 15.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride, m.p. 212°-214°. The free base melts at 43°-45°. After completion of the addition (0.5 hour) the solution obtained are added dropwise at 0° The acidic mixture is filtered the neutral constituents remaining are removed by extraction with chloroform extracted several times with chloroform The chloroform extracts are dried concentrated is recrystallized from ethanol/ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 23 ml (0.17 mol) of triethylamine are added dropwise at 0° to a suspension of 23.5 g (0.15 mol) of 4-chlorobenzoic acid and 15 ml (0.16 mol) of ethyl chloroformate in 200 ml of chloroform. After completion of the addition (0.5 hour), the solution obtained is added dropwise at 0° to a solution of 50 ml (0.75 mol) of ethylenediamine in 100 ml of chloroform. After completion of the reaction, 115 ml of concentrated hydrochloric acid are added dropwise at 0°. The acidic mixture is filtered and the neutral constituents remaining are removed by extraction with chloroform. The aqueous phase is then made alkaline with sodium hydroxide solution and extracted several times with chloroform. The chloroform extracts are dried and concentrated. The residue is converted into the hydrochloride which is recrystallized from ethanol/ether. There are obtained 15.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride, m.p. 212°-214°. The free base melts at 43°-45°. After completion of the addition (0.5 hour) the solution obtained are added dropwise at 0° The acidic mixture is filtered the neutral constituents remaining are removed by extraction with chloroform extracted several times with chloroform The chloroform extracts are dried concentrated is recrystallized from ethanol/ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2.8 g of t-butyl [2-(4-chlorobenzamido)ethyl]carbamate in 50 ml of formic acid is left to stand at room temperature for 1.5 hours. The mixture is then concentrated to dryness, and the residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume). The solution is concentrated, the residue is evaporated twice with ethanol/benzene and then recrystallized from ethanol. There are obtained 2.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride which is identical with the product obtained in Example 1. The mixture is then concentrated to dryness the residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume) The solution is concentrated the residue is evaporated twice with ethanol/benzene recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2.8 g of t-butyl [2-(4-chlorobenzamido)ethyl]carbamate in 50 ml of formic acid is left to stand at room temperature for 1.5 hours. The mixture is then concentrated to dryness, and the residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume). The solution is concentrated, the residue is evaporated twice with ethanol/benzene and then recrystallized from ethanol. There are obtained 2.1 g of N-(2-aminoethyl)-4-chlorobenzamide hydrochloride which is identical with the product obtained in Example 1. The mixture is then concentrated to dryness the residue is dissolved in 50 ml of hydrochloric acid(l:l; volume/volume) The solution is concentrated the residue is evaporated twice with ethanol/benzene recrystallized from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 18.5 g of ethyl 4-chlorobenzoate and 24 g of ethylenediamine are stirred at 130° for 17 hours. The mixture is cooled to room temperature, evaporated, and the residue is treated with 200 ml of ethyl acetate. The insoluble N,N'-ethylenebis(4-chlorobenzamide) (2.3 g), m.p. 266°-268°, is filtered off under suction, and the filtrate is washed three times with 50 ml of water each time and evaporated. The residue is treated with 100 ml of 1N hydrochloric acid, the insoluble N,N'-ethylenebis(4-chlorobenzamide) (1.0 g) is filtered off under suction, and the filtrate is evaporated to dryness. The residue is then evaporated twice with 100 ml of ethanol/benzene each time and recrystallized from ethanol/ether. There are obtained 13.7 g of N-(2-amino-ethyl)-4-chlorobenzamide hydrochloride, m.p. 216°-217°. evaporated the residue is treated with 200 ml of ethyl acetate The insoluble N,N'-ethylenebis(4-chlorobenzamide) (2.3 g), m.p. 266°-268°, is filtered off under suction the filtrate is washed three times with 50 ml of water each time evaporated The residue is treated with 100 ml of 1N hydrochloric acid the insoluble N,N'-ethylenebis(4-chlorobenzamide) (1.0 g) is filtered off under suction the filtrate is evaporated to dryness The residue is then evaporated twice with 100 ml of ethanol/benzene each time recrystallized from ethanol/ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 18.5 g of ethyl 4-chlorobenzoate and 24 g of ethylenediamine are stirred at 130° for 17 hours. The mixture is cooled to room temperature, evaporated, and the residue is treated with 200 ml of ethyl acetate. The insoluble N,N'-ethylenebis(4-chlorobenzamide) (2.3 g), m.p. 266°-268°, is filtered off under suction, and the filtrate is washed three times with 50 ml of water each time and evaporated. The residue is treated with 100 ml of 1N hydrochloric acid, the insoluble N,N'-ethylenebis(4-chlorobenzamide) (1.0 g) is filtered off under suction, and the filtrate is evaporated to dryness. The residue is then evaporated twice with 100 ml of ethanol/benzene each time and recrystallized from ethanol/ether. There are obtained 13.7 g of N-(2-amino-ethyl)-4-chlorobenzamide hydrochloride, m.p. 216°-217°. evaporated the residue is treated with 200 ml of ethyl acetate The insoluble N,N'-ethylenebis(4-chlorobenzamide) (2.3 g), m.p. 266°-268°, is filtered off under suction the filtrate is washed three times with 50 ml of water each time evaporated The residue is treated with 100 ml of 1N hydrochloric acid the insoluble N,N'-ethylenebis(4-chlorobenzamide) (1.0 g) is filtered off under suction the filtrate is evaporated to dryness The residue is then evaporated twice with 100 ml of ethanol/benzene each time recrystallized from ethanol/ether