Imidazole → 1H-Imidazole-1-propanamine

Following the procedure of Schwan, J. Het. Chem. 4, 633 (1967), 25 ml. of acrylonitrile was heated to 70° C. A 13.6 g. portion of imidazole was added and the mixture was gradually heated to 90°-100° C. and maintained at that temperature for 3 hours. The mixture was then concentrated in vacuo to remove excess acrylonitrile, taken up in methanol and reconcentrated. The concentrate was added to 150 ml. of methanol, 100 ml. of concentrated ammonium hydroxide and 8 g. of Raney nickel catalyst in a Parr apparatus and subjected to hydrogenation at an initial pressure of 53 psi. After approximately 6 hours and the uptake of 32 psi. of hydrogen, the mixture was filtered. The filtrate was concentrated to remove the solvent, then concentrated once from ethanol, giving 1H-imidazole-1-propanamine as an oil. When this was added to 250 ml. of methanolic hydrogen chloride, concentrated to remove the solvent, boiled with 100 ml. of ethanol and then refrigerated, 20.3 g. of 1H-imidazole-1-propanamine dihydrochloride was obtained as a tan solid, m.p. 146°-150° C.

1. temperaturethe mixture was gradually heated to 90°-100° C.
2. temperaturemaintained at that temperature for 3 hours
3. concentrationThe mixture was then concentrated in vacuo
4. customto remove excess acrylonitrile
5. additionThe concentrate was added to 150 ml
6. filtrationof hydrogen, the mixture was filtered
7. concentrationThe filtrate was concentrated
8. customto remove the solvent
9. concentrationconcentrated once from ethanol

ORD record

ord-d7efaf65126f4cf8ba8359046b716d19

Source dataset

uspto-grants-1984_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04489089