5-(dimethylamino)pentanenitrile

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

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

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

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

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

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

Procedure: A mixture of dimethylamine (4 mL, 40% in water) and 5-bromo-pentanenitrile (2.3 mL, 20 mmol) is stirred for 24 h. The resulting reaction mixture is diluted with sodium hydroxide solution (10 mL, 5M) and extracted with ether. The ether extract is dried over K2CO3 and concentrated under reduced pressure to give an oil (1.5 g) which is used without further purification. The resulting reaction mixture extracted with ether The ether extract is dried over K2CO3 concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (0° C.) solution of lithium aluminum hydride (8 ml, 0.5M in ether) is added, slowly, a solution of 5-(dimethylamino)-pentanenitrile (126 mg, 1 mmol, reference example 94a) in ether (1 mL). On complete addition, the cold bath is removed and stirring continued for 2 h. The reaction mixture is then cooled to 0° C. and quenched by dropwise addition of water (160 mL), sodium hydroxide solution (160 mL, 5M), then a further portion of water (160 mL). The resulting mixture is filtered through celite and the filtrate concentrated under reduced pressure to give an oil which is used without further purification. is added On complete addition the cold bath is removed quenched by dropwise addition of water (160 mL), sodium hydroxide solution (160 mL, 5M) The resulting mixture is filtered through celite the filtrate concentrated under reduced pressure to give an oil which is used without further purification