2-(4-chlorophenyl)propane-1,3-diamine

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

Procedure: 30 g (0.1165 mol) of 2-(4-chlorophenyl)propane-1,3-diamine dihydrochloride are dissolved in the minimum quantity of water, NaOH is added until the pH is 11, the mixture is extracted with 4×100 ml of chloroform, the chloroform phase is washed with 50 ml of water, dried over MgSO4 and filtered, and the filtrate is evaporated to dryness to give 20.8 g (0.1127 mol) of 2-(4-chlorophenyl)propane-1,3-diamine. is added until the pH is 11 the mixture is extracted with 4×100 ml of chloroform the chloroform phase is washed with 50 ml of water dried over MgSO4 filtered the filtrate is evaporated to dryness

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

Procedure: A solution of benzaldehyde (0.0056 mL, 0.056 mmol) and 2-(4-chlorophenyl)propane-1,3-diamine (10.8 mg, 0.059 mmol) in 0.7 mL t-BuOH was heated at 70° C. for 15 min. The reaction mixture was cooled to rt and treated with K2CO3 (38.5 mg, 0.279 mmol) and iodine (17.7 mg, 0.070 mmol). The reaction mixture was stirred for 5 min at rt and then heated to 70° C. for 2.5 hours. The reaction mixture was cooled to rt and saturated aqueous Na2SO3 was added drop-wise until the color changed from orange to yellow. The reaction mixture was partitioned between EtOAc and aqueous Na2CO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and concentrated. The residue was chromatographed using basic aluminum oxide column and eluting with 5% MeOH/CHCl3 to give the title compound as an off-white solid (13.1 mg, 87%). 1H NMR (CDCl3) δ: 7.67-7.70 (m, 2H), 7.36-7.43 (m, 3H), 7.30-7.32 (m, 2H), 7.14-7.18 (m, 2H), 3.70 (dd, J=12.9, 4.4 Hz, 2H), 3.50 (dd, J=13.5, 10.3 Hz, 2H), 3.00 (tt, J=10.0, 4.8 Hz, 1H). heated to 70° C. for 2.5 hours The reaction mixture was cooled to rt The reaction mixture was partitioned between EtOAc and aqueous Na2CO3 solution the EtOAc layer washed with H2O, brine dried with anhydrous Na2SO4 concentrated The residue was chromatographed eluting with 5% MeOH/CHCl3

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

Procedure: According to the procedure described in Eur. J. Org. Chem. 2010, 3, 484-493, a mixture of 1-chloro-4-[2-nitro-1-(nitromethyl)ethyl]benzene (80 mg, 0.327 mmol) and 18 mg platinum (IV) oxide in 5 mL MeOH contained in a pressure tube was reacted under 50 PSI hydrogen. After 15 hours the mixture was filtered through Celite, rinsed with MeOH and evaporated to give a quantitative yield (60 mg) of the title compound as a yellow-orange oil. 1H NMR (CD3OD) δ: 7.34-7.38 (m, 2H), 7.21-7.29 (m, 2H), 2.88-2.98 (m, 2H), 2.73-2.86 (m, 3H). contained in a pressure tube After 15 hours the mixture was filtered through Celite rinsed with MeOH evaporated

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

Procedure: According to the procedure described in Eur. J. Org. Chem. 2010, 3, 484-493, a mixture of 1-chloro-4-[2-nitro-1-(nitromethyl)ethyl]benzene (80 mg, 0.327 mmol) and 18 mg platinum (IV) oxide in 5 mL MeOH contained in a pressure tube was reacted under 50 PSI hydrogen. After 15 hours the mixture was filtered through Celite, rinsed with MeOH and evaporated to give a quantitative yield (60 mg) of the title compound as a yellow-orange oil. 1H NMR (CD3OD) δ: 7.34-7.38 (m, 2H), 7.21-7.29 (m, 2H), 2.88-2.98 (m, 2H), 2.73-2.86 (m, 3H). contained in a pressure tube After 15 hours the mixture was filtered through Celite rinsed with MeOH evaporated

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

Procedure: 30 g (0.1165 mol) of 2-(4-chlorophenyl)propane-1,3-diamine dihydrochloride are dissolved in the minimum quantity of water, NaOH is added until the pH is 11, the mixture is extracted with 4×100 ml of chloroform, the chloroform phase is washed with 50 ml of water, dried over MgSO4 and filtered, and the filtrate is evaporated to dryness to give 20.8 g (0.1127 mol) of 2-(4-chlorophenyl)propane-1,3-diamine. is added until the pH is 11 the mixture is extracted with 4×100 ml of chloroform the chloroform phase is washed with 50 ml of water dried over MgSO4 filtered the filtrate is evaporated to dryness