Imidazole → 1H-Imidazole-1-propanamine

A mixture of 41 g. of imidazole and 75 ml. of acrylonitrile was heated on a steam bath for 3 hours, then concentrated under reduced pressure to remove excess acrylonitrile. A 300 ml. portion of methanol was added to the residue together with 100 ml. of concentrated ammonium hydroxide and 8 g. of Raney nickel catalyst. This mixture was hydrogenated in a Parr apparatus until hydrogen uptake ceased and then filtered giving a light green liquid. A 300 ml. portion of tetrahydrofuran was added to this liquid and the mixture filtered through diatomaceous earth. The filtrate was concentrated twice from toluene, giving 75.2 g. of the desired intermediate as a clear oil.

1. additionA mixture of 41 g
2. concentrationconcentrated under reduced pressure
3. customto remove excess acrylonitrile
4. additionportion of methanol was added to the residue together with 100 ml
5. filtrationfiltered
6. customgiving a light green liquid
7. filtrationthe mixture filtered through diatomaceous earth
8. concentrationThe filtrate was concentrated twice from toluene
9. customgiving 75.2 g

ORD record

ord-46b4692a6b094e2b962dc758cfa78bad

Source dataset

uspto-grants-1986_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04576957