1,4-benzenediacetonitrile

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

Procedure: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (2 g, 12.8 mmol), acetic acid (95 mL), and platinum oxide (0.25 g) and the mixture was heated at 60° C. under 60 psi (413.7 kPa) of hydrogen gas for 6 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)cyclohexyl]ethylamine, (3.7 g, 100%) as an oil. Electron spray M.S. 171 (M*+1). Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum

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

Procedure: Scheme I, step B′: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (10 g, 64.02 mmol), liquid ammonia (25 mL), and W4-W6 range (medium range activity) Raney Nickel (1.25 g) in methanol (125 mL), and the mixture was heated at 100° C. under 300 psi (2068 kPa) of hydrogen gas for 10 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)phenyl]ethylamine, (10.3 g, 98%) as an oil. Electron spray M.S. 165 (M*+H). Scheme I, step B′: Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum

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

Procedure: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (2 g, 12.8 mmol), acetic acid (95 mL), and platinum oxide (0.25 g) and the mixture was heated at 60° C. under 60 psi (413.7 kPa) of hydrogen gas for 6 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)cyclohexyl]ethylamine, (3.7 g, 100%) as an oil. Electron spray M.S. 171 (M*+1). Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum

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

Procedure: Scheme I, step B′: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (10 g, 64.02 mmol), liquid ammonia (25 mL), and W4-W6 range (medium range activity) Raney Nickel (1.25 g) in methanol (125 mL), and the mixture was heated at 100° C. under 300 psi (2068 kPa) of hydrogen gas for 10 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)phenyl]ethylamine, (10.3 g, 98%) as an oil. Electron spray M.S. 165 (M*+H). Scheme I, step B′: Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum

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

Procedure: A solution of 130 grams (2.65 moles) sodium cyanide in 200 ml of water was placed in a four-necked flask, equipped with a thermowell, mechanical stirrer, electrically heated addition funnel and a condenser. A solution of 200 grams (1.15 mole) of p-xylylene chloride in 200 ml of dimethyl formamide was added dropwise with constant stirring and such a rate as to maintain the reaction temperature at 60°-65°C. The p-xylylene chloride solution was maintained at about 60°C. to prevent solid precipitation. The reaction was exothermic and addition took 2 hours. At the completion of the addition, the temperature was maintained by external heating for an additional hour. The mixture was then poured into 2 liters of water. The precipitated solid was filtered and washed with an additional liter of water. The product yield was 85% (ca. 152 g.) of para-phenylene diacetonitrile having a melting point of about 95°-97°C. equipped with a thermowell, mechanical stirrer electrically heated addition funnel and a condenser such a rate as to maintain the reaction temperature at 60°-65°C solid precipitation addition At the completion of the addition the temperature was maintained by external heating for an additional hour The mixture was then poured into 2 liters of water The precipitated solid was filtered washed with an additional liter of water

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

Procedure: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (2 g, 12.8 mmol), acetic acid (95 mL), and platinum oxide (0.25 g) and the mixture was heated at 60° C. under 60 psi (413.7 kPa) of hydrogen gas for 6 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)cyclohexyl]ethylamine, (3.7 g, 100%) as an oil. Electron spray M.S. 171 (M*+1). Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum

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

Procedure: Scheme I, step B′: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (10 g, 64.02 mmol), liquid ammonia (25 mL), and W4-W6 range (medium range activity) Raney Nickel (1.25 g) in methanol (125 mL), and the mixture was heated at 100° C. under 300 psi (2068 kPa) of hydrogen gas for 10 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)phenyl]ethylamine, (10.3 g, 98%) as an oil. Electron spray M.S. 165 (M*+H). Scheme I, step B′: Into a 250 mL reduction vessel were placed filtered through a Celite® cake the filtrate was concentrated under reduced vacuum