tert-butyl N-[2-(2-aminoanilino)ethyl]carbamate

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

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

Procedure: 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol) was added to a solution of tert-butyl 2-(2-aminophenylamino)ethylcarbamate (0.56 g, 2.23mmol) in dichloromethane (15 mL) and stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3) to give the title compound (230 mg, 37%). the mixture was extracted with dichloromethane (3×50 mL) The combined organic layers were washed with brine (50 mL) dried over anhydrous sodium sulfate filtered The solvent was removed the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3)

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

Procedure: 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol) was added to a solution of tert-butyl 2-(2-aminophenylamino)ethylcarbamate (0.56 g, 2.23mmol) in dichloromethane (15 mL) and stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3) to give the title compound (230 mg, 37%). the mixture was extracted with dichloromethane (3×50 mL) The combined organic layers were washed with brine (50 mL) dried over anhydrous sodium sulfate filtered The solvent was removed the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3)

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

Procedure: A mixture of tert-butyl 2-(2-nitrophenylamino)ethylcarbamate (400 mg) and palladium (10% on activated carbon, 20 mg) in ethanol (50 mL) was stirred under hydrogen (1 atm) for 5 h. The mixture was filtered through Celite and washed with methanol. The solvent was removed and the product was used in the next step without further purification. The mixture was filtered through Celite washed with methanol The solvent was removed the product was used in the next step without further purification

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

Procedure: 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol) was added to a solution of tert-butyl 2-(2-aminophenylamino)ethylcarbamate (0.56 g, 2.23 mmol) in dichloromethane (15 mL) and stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3) to give the title compound (230 mg, 37%). the mixture was extracted with dichloromethane (3×50 mL) The combined organic layers were washed with brine (50 mL) dried over anhydrous sodium sulfate filtered The solvent was removed the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3)

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

Procedure: A mixture of tert-butyl 2-(2-nitrophenylamino)ethylcarbamate (400 mg) and palladium (10% on activated carbon, 20 mg) in ethanol (50 mL) was stirred under hydrogen (1 atm) for 5 h. The mixture was filtered through Celite and washed with methanol. The solvent was removed and the product was used in the next step without further purification. The mixture was filtered through Celite washed with methanol The solvent was removed the product was used in the next step without further purification

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

Procedure: A mixture of tert-butyl 2-(2-nitrophenylamino)ethylcarbamate (400 mg) and palladium (10% on activated carbon, 20 mg) in ethanol (50 mL) was stirred under hydrogen (1 atm) for 5 h. The mixture was filtered through Celite and washed with methanol. The solvent was removed and the product was used in the next step without further purification. The mixture was filtered through Celite washed with methanol The solvent was removed the product was used in the next step without further purification

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

Procedure: A mixture of [2-(2-aminophenylamino)ethyl]carbamic acid t-butyl ester (3.85 g, 15.3 mmol) and 1,1-carbonyldiimidazole (CDI) (2.73 g, 16.8 mmol) in DMF are heated at 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, 1:1 CH2Cl2: EtOAc as eluent) to give the title compound as a brown solid, 2.4 g (56% yield), identified by HPLC and mass spectral analyses. are heated at 110°-120° C. until reaction 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, 1:1 CH2Cl2: EtOAc as eluent)

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

Procedure: A mixture of [2-(2-nitrophenylamino)ethyl]carbamic acid t-butyl ester (6 g, 21.3 mmol) and Raney-Nickel (0.5 g) in methanol is treated dropwise with hydrazine (0.8 mL, 25 mmol), stirred at room temperature until reaction is complete by TLC, treated with Celite and MgSO4 and filtered. The filtercake is washed with methanol. The filtrates are combined and concentrated in vacuo to give the title compound as a brown oil, 3.85 g (72% yield), identified by HPLC and mass spectral analyses. filtered The filtercake is washed with methanol concentrated in vacuo

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

Procedure: 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol) was added to a solution of tert-butyl 2-(2-aminophenylamino)ethylcarbamate (0.56 g, 2.23mmol) in dichloromethane (15 mL) and stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3) to give the title compound (230 mg, 37%). the mixture was extracted with dichloromethane (3×50 mL) The combined organic layers were washed with brine (50 mL) dried over anhydrous sodium sulfate filtered The solvent was removed the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3)

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

Procedure: A mixture of tert-butyl 2-(2-nitrophenylamino)ethylcarbamate (400 mg) and palladium (10% on activated carbon, 20 mg) in ethanol (50 mL) was stirred under hydrogen (1 atm) for 5 h. The mixture was filtered through Celite and washed with methanol. The solvent was removed and the product was used in the next step without further purification. The mixture was filtered through Celite washed with methanol The solvent was removed the product was used in the next step without further purification