2-N-[3-(dimethylamino)propyl]benzene-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: 10.1 g. of o-nitrobromobenzene is reacted, analogously to Example 27, with 5.1 g. of 3-dimethylaminopropylamine, thus obtaining 6 g. of 2-(3-dimethylaminopropylamino)-nitrobenzene, b.p. 138°-141° C. at 0.1 mm Hg. By reducing 3.5 g. of this compound with hydrazine - palladium, 2.9 g. of 2-(3-dimethylaminopropylamino)-aniline is obtained in the form of an oil. 400 mg. of this diamine is reacted with the ethyl ester of 5-nitro-1-methyl-2-imidazolyl-iminocarboxylic acid, as described in Example 1, to obtain 407 mg. of 1-(3-dimethylaminopropyl)-2-(5-nitro-1-methyl-2-imidazolyl)-benzimidazole hydrochloride, m.p. 250° C.

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

Procedure: Triethylamine (0.62 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (0.78 g) in chloroform (4 ml) and then stearoyl chloride (1.22 g) was added thereto while being cooled with ice. After being stirred for 2 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (3.33 ml) was added to a solution containing the residue (1.93 g) in n ethanol (20 ml). After being stirred for 5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (1.73 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1), thereby yielding the entitled compound (1.53 g) as pale brown wax. while being cooled with ice washed with saturated sodium hydrogencarbonate aqueous solution and water successively dried over sodium sulfate anhydride concentrated Concentrated hydrochloric acid (3.33 ml) was added to a solution containing the residue (1.93 g) in n ethanol (20 ml) After being stirred for 5 hours at 90° C. the reaction mixture was concentrated The residue, with ethyl acetate added was washed with 1N sodium hydroxide aqueous solution and saturated brine successively dried over sodium sulfate anhydride concentrated The residue (1.73 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1)

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

Procedure: Triethylamine (0.80 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.00 g) in chloroform (10 ml) and then palmitoyl chloride (1.58 ml) was added thereto while being cooled with ice. After being stirred for 2.5 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium bydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.3 ml) was added to a solution containing the residue (2.25 g) in ethanol (23 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.21 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=30:1), thereby yielding the entitled compound (1.44 g) as yellow syrup. while being cooled with ice washed with saturated sodium bydrogencarbonate aqueous solution and water successively dried over sodium sulfate anhydride concentrated Concentrated hydrochloric acid (4.3 ml) was added to a solution containing the residue (2.25 g) in ethanol (23 ml) After being stirred for 1.5 hours at 90° C. the reaction mixture was concentrated The residue, with ethyl acetate added was washed with 1N sodium hydroxide aqueous solution and saturated brine successively dried over sodium sulfate anhydride concentrated The residue (2.21 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=30:1)

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

Procedure: Triethylamine (0.80 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.00 g) in chloroform (10 ml), and then tetradecanoyl chloride (1.42 ml) was added thereto while being cooled with ice. After being stirred for 3 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.3 ml) was added to a solution containing the residue (2.29 g) in ethanol (23 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.18 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1), thereby yielding the entitled compound (1.38 g) as pale brown wax. while being cooled with ice washed with saturated sodium hydrogencarbonate aqueous solution and water successively dried over sodium sulfate anhydride concentrated Concentrated hydrochloric acid (4.3 ml) was added to a solution containing the residue (2.29 g) in ethanol (23 ml) After being stirred for 1.5 hours at 90° C. the reaction mixture was concentrated The residue, with ethyl acetate added was washed with 1N sodium hydroxide aqueous solution and saturated brine successively dried over sodium sulfate anhydride concentrated The residue (2.18 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=50:1)

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

Procedure: Triethylamine (0.85 ml) was added to a solution containing N-[3-(dimethylamino)propyl]-1,2-benzenediamine (1.06 g) in chloroform (11 ml) and then dodecanoyl chloride (1.28 ml) was added thereto while being cooled with ice. After being stirred for 3 hours at room temperature, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (4.6 ml) was added to a solution containing the residue (2.23 g) in ethanol (23 ml). After being stirred for 1.5 hours at 90° C., the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (2.14 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=60:1), thereby yielding the entitled compound (1.33 g) as pale brown wax. while being cooled with ice washed with saturated sodium hydrogencarbonate aqueous solution and water successively dried over sodium sulfate anhydride concentrated Concentrated hydrochloric acid (4.6 ml) was added to a solution containing the residue (2.23 g) in ethanol (23 ml) After being stirred for 1.5 hours at 90° C. the reaction mixture was concentrated The residue, with ethyl acetate added was washed with 1N sodium hydroxide aqueous solution and saturated brine successively dried over sodium sulfate anhydride concentrated The residue (2.14 g) was purified by silica gel column chromatography (silica gel 50 g, chloroform:methanol=60:1)

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

Procedure: 10% of palladium-carbon (0.18 g) was added to a solution containing N1,N1-dimethyl-N3-(2-nitrophenyl)-1,3-propanediamine (0.90 g) in ethanol (9 ml) and stirred for 2.5 hours under a hydrogen gas atmosphere at room temperature. After the catalyst was removed out by filtration, the filtrate was concentrated, thereby yielding the entitled compound (0.78 g) as reddish brown oil. After the catalyst was removed out by filtration the filtrate was concentrated

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

Procedure: 10.1 g. of o-nitrobromobenzene is reacted, analogously to Example 27, with 5.1 g. of 3-dimethylaminopropylamine, thus obtaining 6 g. of 2-(3-dimethylaminopropylamino)-nitrobenzene, b.p. 138°-141° C. at 0.1 mm Hg. By reducing 3.5 g. of this compound with hydrazine - palladium, 2.9 g. of 2-(3-dimethylaminopropylamino)-aniline is obtained in the form of an oil. 400 mg. of this diamine is reacted with the ethyl ester of 5-nitro-1-methyl-2-imidazolyl-iminocarboxylic acid, as described in Example 1, to obtain 407 mg. of 1-(3-dimethylaminopropyl)-2-(5-nitro-1-methyl-2-imidazolyl)-benzimidazole hydrochloride, m.p. 250° C.