2-N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine (2.0 g, 14 mmol) and 10% palladium on carbon, wet, 50% water (3.0 g) were combined under nitrogen. 30 mL MeOH was added via syringe, and the atmosphere was replaced with hydrogen from a balloon. The reaction was stirred rapidly for 20 h, at which point the reaction was flushed with nitrogen, and filtered through a pad of Celite®, and concentrated in vacuo to give N1-(2-(dimethylamino)ethyl)benzene-1,2-diamine as a red-brown solid. This material was used without further purification. MS m/z=180 [M+H]+. Calc'd for C10H17N3: 179.3. was flushed with nitrogen filtered through a pad of Celite® concentrated in vacuo

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

Procedure: N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine (2.0 g, 14 mmol) and 10% palladium on carbon, wet, 50% water (3.0 g) were combined under nitrogen. 30 mL MeOH was added via syringe, and the atmosphere was replaced with hydrogen from a balloon. The reaction was stirred rapidly for 20 h, at which point the reaction was flushed with nitrogen, and filtered through a pad of Celite®, and concentrated in vacuo to give N1-(2-(dimethylamino)ethyl)benzene-1,2-diamine as a red-brown solid. This material was used without further purification. MS m/z=180 [M+H]+. Calc'd for C10H17N3: 179.3. was flushed with nitrogen filtered through a pad of Celite® concentrated in vacuo

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

Procedure: N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine (2.0 g, 14 mmol) and 10% palladium on carbon, wet, 50% water (3.0 g) were combined under nitrogen. 30 mL MeOH was added via syringe, and the atmosphere was replaced with hydrogen from a balloon. The reaction was stirred rapidly for 20 h, at which point the reaction was flushed with nitrogen, and filtered through a pad of Celite®, and concentrated in vacuo to give N1-(2-(dimethylamino)ethyl)benzene-1,2-diamine as a red-brown solid. This material was used without further purification. MS m/z=180 [M+H]+. Calc'd for C10H17N3: 179.3. was flushed with nitrogen filtered through a pad of Celite® concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of N,N-dimethyl-N′-(2-nitrophenyl)ethane-1,2-diamine (3.83 g, 18.3 mmol) and Raney-Nickel (0.5 g) in methanol is treated dropwise with hydrazine (5 mL), stirred at room temperature until reaction is complete by TLC, treated with Celite and MgSO4 and filtered. The filtercake is washed with methanol. The combined filtrate is concentrated in vacuo to give the title compound as a brown oil, 3.11 g (94% yield), identified by HPLC and mass spectral analyses. filtered The filtercake is washed with methanol The combined filtrate is concentrated in vacuo

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

Procedure: A mixture of N-[2-(dimethylamino)ethyl]benzene-1,2-diamine (3.11 g, 17.3 mmol) and 1,1-carbonyldiimidazole (CDI) (3.2 g, 19 mmol) are heated in DMF to 110°-120° C. until reaction is complete by TLC, cooled and extracted with EtOAc. The combined extracts are washed with water, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, 94:5:1 CH2Cl2, methanol, concentrated NH4OH as eluent) to give the title compound as a dark purple solid, 3.03 g (85% yield), identified by HPLC and mass spectral analyses. cooled extracted with EtOAc The combined extracts are washed with water dried over MgSO4 concentrated in vacuo The resultant residue is purified by flash chromatography (silica gel, 94:5:1 CH2Cl2, methanol, concentrated NH4OH as eluent)

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

Procedure: Triethylamine (2.25 ml) was added to a suspension containing n-docosanoic acid (4.930 g) in chloroform (50 ml), and then ethyl chlorocarbonate (1.52 ml) was added thereto while being cooled with ice. After being stirred for 1.5 hours, a solution containing N-[2-(dimethylamino)ethyl]-1,2-benzenediamine (2.593 g) in chloroform (13 ml). After being stirred for 2.5 hours while being cooled with ice, the reaction mixture was diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (12.1 ml) was added to a solution containing the residue (8.644 g) in ethanol (87 ml). After being stirred for 2.5 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 (6.90 g) was purified by silica gel column chromatography (silica gel 150 g, chloroform:methanol=60:1-30:1), thereby yielding the entitled compound (4.604 g) as pale yellow solid. while being cooled with ice After being stirred for 2.5 hours while being cooled with ice washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively dried over sodium sulfate anhydride concentrated Concentrated hydrochloric acid (12.1 ml) was added to a solution containing the residue (8.644 g) in ethanol (87 ml) After being stirred for 2.5 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 (6.90 g) was purified by silica gel column chromatography (silica gel 150 g, chloroform:methanol=60:1-30:1)

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

Procedure: N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine (2.0 g, 14 mmol) and 10% palladium on carbon, wet, 50% water (3.0 g) were combined under nitrogen. 30 mL MeOH was added via syringe, and the atmosphere was replaced with hydrogen from a balloon. The reaction was stirred rapidly for 20 h, at which point the reaction was flushed with nitrogen, and filtered through a pad of Celite®, and concentrated in vacuo to give N1-(2-(dimethylamino)ethyl)benzene-1,2-diamine as a red-brown solid. This material was used without further purification. MS m/z=180 [M+H]+. Calc'd for C10H17N3: 179.3. was flushed with nitrogen filtered through a pad of Celite® concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir: