Ethanamine, N-(4-pyridinylmethylene)- synthesis

Yield:-

Reaction Conditions:

in ethanol;water; for 0.5 h;Cooling with ice;

Steps:

7.1 N-(4-pyridinylmethyl)ethylamine (VI₁):

15.70g (0.147mol) of 4-pyridine-formaldehyde was dissolved in 200mL of ethanol, added under stirring in cold-water-bath with 21g (0.296mol) of 65-70% ethylamine aqueous solution, reacted for 0.5h, monitored with TLC until the reaction was almost completed. Added carefully with 5.6g (0.148mol) of sodium borohydride in several batches, small amount in each batch, after the end of addition, added with 30mL of water, reacted overnight (20h), the reaction was completed according to TLC monitoring. Evaporated to remove solvent, added with water, extracted with dichloromethane, washed with water and saturated saline in order, dried with anhydrous sodium sulfate, evaporated to remove solvent to obtain yellow thick liquid, 30g, crude yield 73.4%.

References:

EP2586780,2013,A1 Location in patent:Paragraph 0059