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

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

Procedure: N-(2-Aminoethyl)-2-chlorobenzamide hydrochloride was suspended in dichloromethane and stirred with triethylamine and methanesulfonyl chloride to obtain 2-chloro-N-{2-[(methylsulfonyl)amino]ethyl}benzamide.

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

Procedure: tert-Butyl {2-[(2-chlorobenzoyl)amino]ethyl}carbamate was dissolved in dioxane and a 4M hydrogen chloride dioxane solution was added thereto. The whole was stirred at room temperature to obtain N-(2-aminoethyl)-2-chlorobenzamide hydrochloride.

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

Procedure: 22.1 ml (0.16 mol) of triethylamine are added dropwise at 10° to a suspension of 23.5 g (0.15 mol) of 2-chlorobenzoic acid in 200 ml of chloroform. 14.8 ml (0.155 mol) of ethyl chloroformate are then added dropwise at the same temperature. After completion of the addition (1 hour), the mixture is poured on to ice/water. The chloroform phase is separated, dried over magnesium sulfate and gently concentrated to about 60 ml. The thus-obtained solution is added dropwise at 10° to a solution of 40.1 ml (0.6 mol) of ethylenediamine in 400 ml of chloroform. After completion of the addition, the difficulty soluble neutral constituents are filtered off, the filtrate is concentrated and excess ethylenediamine is removed in a high vacuum. The residue obtained (31.5 g) is converted into the hydrochloride which is purified by recrystallization from ethanol/ether. There are obtained 19.2 g of N-(2-aminoethyl)-2-chlorobenzamide hydrochloride (see Example 6 of German Offenlegungsschrift 2.362.568), m.p. 155°-158°. An analytically pure sample melts at 159°-161°. After completion of the addition (1 hour) The chloroform phase is separated dried over magnesium sulfate gently concentrated to about 60 ml After completion of the addition the difficulty soluble neutral constituents are filtered off the filtrate is concentrated excess ethylenediamine is removed in a high vacuum The residue obtained (31.5 g) is purified by recrystallization from ethanol/ether

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

Procedure: 22.1 ml (0.16 mol) of triethylamine are added dropwise at 10° to a suspension of 23.5 g (0.15 mol) of 2-chlorobenzoic acid in 200 ml of chloroform. 14.8 ml (0.155 mol) of ethyl chloroformate are then added dropwise at the same temperature. After completion of the addition (1 hour), the mixture is poured on to ice/water. The chloroform phase is separated, dried over magnesium sulfate and gently concentrated to about 60 ml. The thus-obtained solution is added dropwise at 10° to a solution of 40.1 ml (0.6 mol) of ethylenediamine in 400 ml of chloroform. After completion of the addition, the difficulty soluble neutral constituents are filtered off, the filtrate is concentrated and excess ethylenediamine is removed in a high vacuum. The residue obtained (31.5 g) is converted into the hydrochloride which is purified by recrystallization from ethanol/ether. There are obtained 19.2 g of N-(2-aminoethyl)-2-chlorobenzamide hydrochloride (see Example 6 of German Offenlegungsschrift 2.362.568), m.p. 155°-158°. An analytically pure sample melts at 159°-161°. After completion of the addition (1 hour) The chloroform phase is separated dried over magnesium sulfate gently concentrated to about 60 ml After completion of the addition the difficulty soluble neutral constituents are filtered off the filtrate is concentrated excess ethylenediamine is removed in a high vacuum The residue obtained (31.5 g) is purified by recrystallization from ethanol/ether

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

Procedure: N-(2-Aminoethyl)-2-chlorobenzamide hydrochloride was suspended in dichloromethane and stirred with triethylamine and methanesulfonyl chloride to obtain 2-chloro-N-{2-[(methylsulfonyl)amino]ethyl}benzamide.

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

Procedure: tert-Butyl {2-[(2-chlorobenzoyl)amino]ethyl}carbamate was dissolved in dioxane and a 4M hydrogen chloride dioxane solution was added thereto. The whole was stirred at room temperature to obtain N-(2-aminoethyl)-2-chlorobenzamide hydrochloride.