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

HRID 1589177Notes

Reaction equation

HRID 1589177 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:4][N:3]=[CH:2]1.O.NN.Cl>C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 13290795N-[4-(imidazol-1-yl)butyl]phthalimide

Product 1

HCID 43794804-(1H-imidazol-1-yl)butan-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.2 mole of 2-[4-(1H-imidazol-1-yl)butyl]-1H-isoindole-1,3(2H)-dione, 0.22 mol. of hydrazine hydrate and 400 ml. of ethanol was heated on the steam bath for 3 hours and then treated with 400 ml. of 3N HCl and 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)-dione were prepared 1H-imidazole-1-pentanamine, 1H-imidazole-1-hexanamine, 1H-imidazole-1-heptanamine and 1H-imidazole-1-octanamine.

Workup

  1. additiontreated with 400 ml
  2. temperatureat reflux for an additional 2 hours
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe mother liquor was concentrated to a low volume
  5. filtrationagain filtered
  6. distillationThe remainder of the volatile material was distilled off
  7. additionthe residue was treated with saturated potassium carbonate solution
  8. extractionThe 1H-imidazole-1-butanamine was extracted into methylene chloride
  9. distillationfurther purified by distillation on a Kugelrohr apparatus
  10. customIn like manner from the appropriate 2-[ω-(1H-imidazol-1-yl)alkyl]-1H-isoindole-1,3(2H)-dione were prepared 1H-imidazole-1-pentanamine, 1H-imidazole-1-hexanamine, 1H-imidazole-1-heptanamine and 1H-imidazole-1-octanamine

Sources & evidence

ORD record
ord-a66940ba668540419140801dc151a1ff
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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