Hydrochloric Acid → 4-(1H-imidazol-1-yl)butan-1-amine

A mixture of 0.2 mole of 2-[4-(1H-imidazol-1-yl)butyl]-1H-isoindole-1,3(2H)-dione, 0.22 mole of hydrazine hydrate and 400 ml of ethanol was heated on a steam bath for 3 hours and then treated with 400 ml of 3N hydrochloric acid and then heated at reflux for an additional 2 hours. The insoluble material was filtered off and the mother liquor was concentrated to a low volume and again filtered. The remainder of the volatile material was distilled off and the residue was treated with saturated potassium carbonate solution. The 1H-imidazole-1-butanamine was extracted into methylene chloride and further purified by distillation on a Kugelrohr apparatus. In like manner from the appropriate 2-[ω-(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones were prepared 1H-imidazole-1-pentanamine; 1H-imidazole-1-hexanamine; 1H-imidazole-1-heptanamine; and 1H-imidazole-1-octanamine.

1. temperaturewas heated on a steam bath for 3 hours
2. temperatureheated
3. temperatureat reflux for an additional 2 hours
4. filtrationThe insoluble material was filtered off
5. concentrationthe mother liquor was concentrated to a low volume
6. filtrationagain filtered
7. distillationThe remainder of the volatile material was distilled off
8. additionthe residue was treated with saturated potassium carbonate solution
9. extractionThe 1H-imidazole-1-butanamine was extracted into methylene chloride
10. distillationfurther purified by distillation on a Kugelrohr apparatus
11. customIn like manner from the appropriate 2-[ω-(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-diones were prepared 1H-imidazole-1-pentanamine

ORD record

ord-761d985aa6e5403480e77267acf11d11

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04555519