2-phenylpropane-1,3-diamine

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained

Conditions: temp:265.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture consisting of 3.25 g of 2-phenyl-1,3-propanediamine (prepared in accordance with Preparation C) and 3.02 g of 2-methyl-2-thiopseudourea sulfate ([CH3SC(NH)NH2 ]2.H2SO4) in a small flask is immersed in a 245° C. oil bath. The temperature is raised to 265° C. when the reaction mixture solidifies. When the reaction mixture melts again, it is stirred for about five minutes then is removed from the oil-bath. The contents are refluxed with 50 ml of methanol until a powder is formed. The mixture is cooled and the solid product is collected on a Buchner-funnel, washed with 30% ether in methanol and is air-dried to give 3.7 g of crude product. Recrystallization from 20 ml of water yields 2.25 g of 2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine sulfate, mp 264°-267° C. then is removed from the oil-bath The contents are refluxed with 50 ml of methanol until a powder is formed The mixture is cooled the solid product is collected on a Buchner-funnel washed with 30% ether in methanol is air-dried to give 3.7 g of crude product Recrystallization from 20 ml of water

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

Procedure: 2-(2-chlorophenyl)1,3-propanediamine, bp 87°-92° C./0.05 mm (di HCl salt, mp 253°-257° C.);

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained

Conditions: temp:265.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture consisting of 3.25 g of 2-phenyl-1,3-propanediamine (prepared in accordance with Preparation C) and 3.02 g of 2-methyl-2-thiopseudourea sulfate ([CH3SC(NH)NH2 ]2.H2SO4) in a small flask is immersed in a 245° C. oil bath. The temperature is raised to 265° C. when the reaction mixture solidifies. When the reaction mixture melts again, it is stirred for about five minutes then is removed from the oil-bath. The contents are refluxed with 50 ml of methanol until a powder is formed. The mixture is cooled and the solid product is collected on a Buchner-funnel, washed with 30% ether in methanol and is air-dried to give 3.7 g of crude product. Recrystallization from 20 ml of water yields 2.25 g of 2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine sulfate, mp 264°-267° C. then is removed from the oil-bath The contents are refluxed with 50 ml of methanol until a powder is formed The mixture is cooled the solid product is collected on a Buchner-funnel washed with 30% ether in methanol is air-dried to give 3.7 g of crude product Recrystallization from 20 ml of water

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained

Conditions: temp:265.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture consisting of 3.25 g of 2-phenyl-1,3-propanediamine (prepared in accordance with Preparation C) and 3.02 g of 2-methyl-2-thiopseudourea sulfate ([CH3SC(NH)NH2 ]2.H2SO4) in a small flask is immersed in a 245° C. oil bath. The temperature is raised to 265° C. when the reaction mixture solidifies. When the reaction mixture melts again, it is stirred for about five minutes then is removed from the oil-bath. The contents are refluxed with 50 ml of methanol until a powder is formed. The mixture is cooled and the solid product is collected on a Buchner-funnel, washed with 30% ether in methanol and is air-dried to give 3.7 g of crude product. Recrystallization from 20 ml of water yields 2.25 g of 2-amino-5-phenyl-1,4,5,6-tetrahydropyrimidine sulfate, mp 264°-267° C. then is removed from the oil-bath The contents are refluxed with 50 ml of methanol until a powder is formed The mixture is cooled the solid product is collected on a Buchner-funnel washed with 30% ether in methanol is air-dried to give 3.7 g of crude product Recrystallization from 20 ml of water

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

Procedure: 2-(2-chlorophenyl)1,3-propanediamine, bp 87°-92° C./0.05 mm (di HCl salt, mp 253°-257° C.);

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

Procedure: In 50 ml of a chloroform solution containing 11.55 g of 1,3-diamino-2-phenylpropane and 1.33 g of triethylamine was added dropwise 30 ml of a chloroform solution containing 3.5 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 10° C. to 20° C. for four hours, and the reaction mixture solution was washed with water and dried with anhydrous potassium carbonate. After the chloroform was distilled therefrom, the residue thus obtained was subjected to a silica gel column chromatography (silica gel: 90 g; solvent: 5% methanol/chloroform (volume ratio)) to give 3.20 g of N-(3-amino-2-phenylpropyl)-5-isoquinolinesulfonamide in a yield of 61%. under cooling with ice the reaction mixture solution was washed with water dried with anhydrous potassium carbonate After the chloroform was distilled the residue thus obtained