Ammonium Hydroxide → 1-Propanamine, 3-butoxy-

Participants

Reaction Conditions

Reaction Steps

The previously prepared butoxypropionitrile (224.8 grams) was combined with Raney nickel (20 grams of 50/50 mixture with water) in a 1-liter stainless steel autoclave along with a premixed ethanol/ammonium hydroxide solution (37.5 grams of ammonium hydroxide and 212.5 grams of ethanol). The addition of the ammonium hydroxide limits the reaction that leads to the formation of by-product dibutoxypropylamine. After purging with nitrogen, the reactor was pressurized with 500 psi of hydrogen and heated to 60° C. After 20 hours at this temperature, the reactor was cooled to room temperature and the product discharged. The product was filtered to remove the Raney nickel and then distilled using a simple Vigreux column to extract the butoxypropylamine. The distillation produced a yield of about 79.5% of product and 18.3% of the secondary amine.

Provenance & Evidence