Methyl 2-chloroacetimidate hydrochloride

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

Procedure: To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Rogers and D. G. Nielson, Chem. Rev., 61, 179 (1961)](8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water three times; dried over magnesium sulfate and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product. The mixture is washed with water three times dried over magnesium sulfate concentrated to an oil The oil is distilled (120°-135° C. at 0.5 mm Hg)

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

Procedure: 8.64 g of 2-oxopiperazine were added to a solution of 12.4 g of methyl 2-chloroacetimidate hydrochloride in 44.8 ml of anhydrous methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, a small amount of insoluble material was filtered off and the solvent was distilled off from the filtrate. Ether was added to the residue, and the precipitated crystals were collected by filtration and washed with ether, giving 18.0 g of 2-(3-oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride. After completion of the reaction a small amount of insoluble material was filtered off the solvent was distilled off from the filtrate Ether was added to the residue the precipitated crystals were collected by filtration washed with ether

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

Procedure: 1.28 g of (3RS)-3-carbamoylpiperidine were added to a solution of 1.44 g of methyl 2-chloroacetimidate hydrochloride in 5 ml of anhydrous methanol, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then worked up in the same manner as in Example 3(1), giving 2.34 g of 2-[(3RS)-3-carbamoylpiperidin-1-yl]-2-iminoethylchloride hydrochloride.

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

Procedure: 2 ml of a methanolic solution containing 1.064 g of 4-methoxyiminopiperidine was added to a solution of 1.195 g of methyl 2-chloroacetimidate hydrochloride in 4 ml of absolute methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off and the concentrate was mixed with anhydrous ether. The crystals which separated out were collected by filtration and washed with ether, giving 1.5 g of 2-(4-methoxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride. After completion of the reaction the solvent was distilled off the concentrate was mixed with anhydrous ether The crystals which separated out were collected by filtration washed with ether

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

Procedure: 2 ml of a methanolic solution containing 1.064 g of 4-methoxyiminopiperidine was added to a solution of 1.195 g of methyl 2-chloroacetimidate hydrochloride in 4 ml of absolute methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off and the concentrate was mixed with anhydrous ether. The crystals which separated out were collected by filtration and washed with ether, giving 1.5 g of 2-(4-methoxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride. After completion of the reaction the solvent was distilled off the concentrate was mixed with anhydrous ether The crystals which separated out were collected by filtration washed with ether

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

Procedure: To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Roger and D. G. Neilson, Chem. Rev., 61, 179 (1961)] (8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water (3X); dried over magnesium sulfate and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product. The mixture is washed with water (3X) dried over magnesium sulfate concentrated to an oil The oil is distilled (120°-135° C. at 0.5 mm Hg)

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

Procedure: To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Rogers and D. G. Nielson, Chem. Rev., 61, 179 (1961)] (8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water (3X); dried over magnesium sulfate and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product. The mixture is washed with water (3X) dried over magnesium sulfate concentrated to an oil The oil is distilled (120°-135° C. at 0.5 mm Hg)

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

Procedure: To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Rogers and D. G. Nielson, Chem. Rev., 61, 179 (1961)] (8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water three times; dried over magnesium sulfate and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product. The mixture is washed with water three times dried over magnesium sulfate concentrated to an oil The oil is distilled (120°-135° C. at 0.5 mm Hg)

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

Procedure: To a solution of aminothiophenol (8.3 g) in methylene chloride at 0° C. is added methyl chloroacetimidate hydrochloride [prepared according to procedures described by R. Rogers and D. G. Nielson, Chem. Rev., 61, 179 (1961)](8.6 g). The reaction is allowed to warm to room temperature while stirring overnight. The mixture is washed with water three times; dried over magnesium sulfate and concentrated to an oil. The oil is distilled (120°-135° C. at 0.5 mm Hg) to give 7.8 g (71% yield) of product. The mixture is washed with water three times dried over magnesium sulfate concentrated to an oil The oil is distilled (120°-135° C. at 0.5 mm Hg)

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

Procedure: 8.64 g of 2-oxopiperazine were added to a solution of 12.4 g of methyl 2-chloroacetimidate hydrochloride in 44.8 ml of anhydrous methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, a small amount of insoluble material was filtered off and the solvent was distilled off from the filtrate. Ether was added to the residue, and the precipitated crystals were collected by filtration and washed with ether, giving 18.0 g of 2-(3-oxopiperazin-1-yl)-2-iminoethylchloride hydrochloride. After completion of the reaction a small amount of insoluble material was filtered off the solvent was distilled off from the filtrate Ether was added to the residue the precipitated crystals were collected by filtration washed with ether

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

Procedure: 1.28 g of (3RS)-3-carbamoylpiperidine were added to a solution of 1.44 g of methyl 2-chloroacetimidate hydrochloride in 5 ml of anhydrous methanol, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then worked up in the same manner as in Example 3(1), giving 2.34 g of 2-[(3RS)-3-carbamoylpiperidin-1-yl]-2-iminoethylchloride hydrochloride.

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

Procedure: 2 ml of a methanolic solution containing 1.064 g of 4-methoxyiminopiperidine was added to a solution of 1.195 g of methyl 2-chloroacetimidate hydrochloride in 4 ml of absolute methanol, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off and the concentrate was mixed with anhydrous ether. The crystals which separated out were collected by filtration and washed with ether, giving 1.5 g of 2-(4-methoxyiminopiperidin-1-yl)-2-iminoethylchloride hydrochloride. After completion of the reaction the solvent was distilled off the concentrate was mixed with anhydrous ether The crystals which separated out were collected by filtration washed with ether