Ammonium Hydroxide → 1H-1,2,4-Triazole-1-propanamine

To a mixture of 3-(1H-1,2,4-triazol-1-yl)-propanenitrile (25 g, 0.204 mol) and Raney-Nickel (5 g, 0.2 w/w, wet) in methanol (300 mL) was added a solution of 25% aqueous NH4OH (75 mL). The above reaction mixture was hydrogenated under pressure (75 psi of hydrogen) for a period of 6 h. The catalyst was then filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was taken up in DCM (150 mL) then triturated 4 times and the combined organic layer was concentrated under reduced pressure to yield 22 g of the title compound as a liquid (85%). The above compound was converted to its hydrochloride using HCl gas in a mixture of ether/methanol (9.5/0.5) to yield 20 g of the product as its dihydrochloride.

1. customThe above reaction mixture
2. filtrationThe catalyst was then filtered off
3. concentrationthe filtrate was concentrated under reduced pressure
4. customThe residue obtained
5. customthen triturated 4 times
6. concentrationthe combined organic layer was concentrated under reduced pressure

ORD record

ord-109b26a88c5b480bbf6f579d0c73ede1

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465736B2