N'-(4-chlorophenyl)-N'-methylethane-1,2-diamine

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

Procedure: 81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 92 mg (0.5 mmol) of N-(4-chloro-phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-indole-7-carboxylic acid and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel, diethyl ether) to yield 140 mg (59%) product as a colorless oil. MS (ISP) 474.4 (M+H)+. The reaction mixture was stirred at rt for 30 min the solvent was evaporated the mixture was stirred at rt over night The product was purified by column chromatography (silica gel, diethyl ether)

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

Procedure: 1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.85 g (10 mmol) of N-(4-chloro -phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 2.97 g (90%) product as a yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.34 (d, 2H), 7.24 (d, 2H), 7.13 (d, 2H), 6.64 (d, 2H), 3.77 (s, 2H), 3.42 (t, 2H), 2.91 (s, 3H), 2.83 (t, 2H), 1.30 (s, 9H). The reaction mixture was stirred at rt over night the solvent was evaporated The reaction mixture was extracted with diethyl ether the organic layer was washed with saturated aqueous NaCl solution dried over sodium sulfate filtered the solvent was evaporated

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

Procedure: 81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 92 mg (0.5 mmol) of N-(4-chloro-phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-indole-7-carboxylic acid and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel, diethyl ether) to yield 140 mg (59%) product as a colorless oil. MS (ISP) 474.4 (M+H)+. The reaction mixture was stirred at rt for 30 min the solvent was evaporated the mixture was stirred at rt over night The product was purified by column chromatography (silica gel, diethyl ether)

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

Procedure: 1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.85 g (10 mmol) of N-(4-chloro -phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 2.97 g (90%) product as a yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.34 (d, 2H), 7.24 (d, 2H), 7.13 (d, 2H), 6.64 (d, 2H), 3.77 (s, 2H), 3.42 (t, 2H), 2.91 (s, 3H), 2.83 (t, 2H), 1.30 (s, 9H). The reaction mixture was stirred at rt over night the solvent was evaporated The reaction mixture was extracted with diethyl ether the organic layer was washed with saturated aqueous NaCl solution dried over sodium sulfate filtered the solvent was evaporated