5,7-dimethyladamantane-1,3-diamine

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

Procedure: Diamide 3 (1.56 g) was added to diethyene glycol (25 mL). The reaction mixture was stirred at 175˜180° C. for 16 h. The brown solution was cooled to room temperature, and water was added (100 mL). The reaction mixture was extracted with a solvent consisting of ethyl acetate (80%) and t-butylmethyl ether (20%) (70 mL×7). The combined organic solvent was washed with water and brine, and dried over sodium sulfate. The solution was concentrated to approximately 20 mL. Anhydrous hydrogen chloride in ethyl acetate was added. The precipitate was filtered. The product was then dissolved in water (10 mL). The product was extracted with ethyl acetate (10 mL×6). Solvent was removed to afford diamine 4 as an off-white solid (767 mg). The reaction mixture was extracted with a solvent The combined organic solvent was washed with water and brine dried over sodium sulfate The solution was concentrated to approximately 20 mL Anhydrous hydrogen chloride in ethyl acetate was added The precipitate was filtered The product was then dissolved in water (10 mL) The product was extracted with ethyl acetate (10 mL×6) Solvent was removed

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

Procedure: Diamide 3 (1.56 g) was added to diethyene glycol (25 mL). The reaction mixture was stirred at 175˜180° C. for 16 h. The brown solution was cooled to room temperature, and water was added (100 mL). The reaction mixture was extracted with a solvent consisting of ethyl acetate (80%) and t-butylmethyl ether (20%) (70 mL×7). The combined organic solvent was washed with water and brine, and dried over sodium sulfate. The solution was concentrated to approximately 20 mL. Anhydrous hydrogen chloride in ethyl acetate was added. The precipitate was filtered. The product was then dissolved in water (10 mL). The product was extracted with ethyl acetate (10 mL×6). Solvent was removed to afford diamine 4 as an off-white solid (767 mg). The reaction mixture was extracted with a solvent The combined organic solvent was washed with water and brine dried over sodium sulfate The solution was concentrated to approximately 20 mL Anhydrous hydrogen chloride in ethyl acetate was added The precipitate was filtered The product was then dissolved in water (10 mL) The product was extracted with ethyl acetate (10 mL×6) Solvent was removed

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

Procedure: Diamide 3 (1.56 g) was added to diethyene glycol (25 mL). The reaction mixture was stirred at 175˜180° C. for 16 h. The brown solution was cooled to room temperature, and water was added (100 mL). The reaction mixture was extracted with a solvent consisting of ethyl acetate (80%) and t-butylmethyl ether (20%) (70 mL×7). The combined organic solvent was washed with water and brine, and dried over sodium sulfate. The solution was concentrated to approximately 20 mL. Anhydrous hydrogen chloride in ethyl acetate was added. The precipitate was filtered. The product was then dissolved in water (10 mL). The product was extracted with ethyl acetate (10 mL×6). Solvent was removed to afford diamine 4 as an off-white solid (767 mg). The reaction mixture was extracted with a solvent The combined organic solvent was washed with water and brine dried over sodium sulfate The solution was concentrated to approximately 20 mL Anhydrous hydrogen chloride in ethyl acetate was added The precipitate was filtered The product was then dissolved in water (10 mL) The product was extracted with ethyl acetate (10 mL×6) Solvent was removed

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

Procedure: Diamide 3 (1.56 g) was added to diethyene glycol (25 mL). The reaction mixture was stirred at 175˜180° C. for 16 h. The brown solution was cooled to room temperature, and water was added (100 mL). The reaction mixture was extracted with a solvent consisting of ethyl acetate (80%) and t-butylmethyl ether (20%) (70 mL×7). The combined organic solvent was washed with water and brine, and dried over sodium sulfate. The solution was concentrated to approximately 20 mL. Anhydrous hydrogen chloride in ethyl acetate was added. The precipitate was filtered. The product was then dissolved in water (10 mL). The product was extracted with ethyl acetate (10 mL×6). Solvent was removed to afford diamine 4 as an off-white solid (767 mg). The reaction mixture was extracted with a solvent The combined organic solvent was washed with water and brine dried over sodium sulfate The solution was concentrated to approximately 20 mL Anhydrous hydrogen chloride in ethyl acetate was added The precipitate was filtered The product was then dissolved in water (10 mL) The product was extracted with ethyl acetate (10 mL×6) Solvent was removed