N-Propylcyclopropanemethylamine synthesis

Yield:26389-60-6 60%

Reaction Conditions:

with hydrogen;Pt/C;Rh/C

Steps:

2 (Pilot Plant)
The nitrogen-purged drop tank is charged with 12.5 lbs of a 60-40 mixture of 5% Pt/C and 5% Rh/C catalyst and 13 lbs (2 gallons) of propionitrile (96% pure). The catalyst is slurried by agitation and dropped into the main vessel. An additional 11 lbs (17 gal) of propionitrile is used to flush any slurry residue into the vessel which is then purged of O₂ with nitrogen. The mole ratio of propionitrile to cyclopropylmethylamine is 1:2.35. When the O₂ level is below 0.5%, the vessel is pressurized to 150 psig with hydrogen. The vessel temperature is maintained at 50°+-2° C. and additional hydrogen is added as consumed to maintain the pressure. WHen the hydrogen uptake ceases, the reaction mixture is heated to 60° C. and held there for 2 hours. The mixture is then cooled to 20° C., the hydrogen is carefully vented and the vessel is flushed with nitrogen. The reaction mass is filtered to remove the catalyst and the filtrate is distilled. 28.1 lbs of cyclopropylmethyl-n-propylamine is recovered in 90% yield, based on the cyclopropylmethylamine content of the starting material and 60% yield based on propionitrile.

References:

Ciba-Geigy Corporation US4264527, 1981, A

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