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

HRID 64849Notes

Reaction equation

HRID 64849 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.N1(CCCCCCCCN2C(=O)C3C(=CC=CC=3)C2=O)C=CN=C1.N1(CCCCCCCCN)C=CN=C1>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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 13290795N-[4-(imidazol-1-yl)butyl]phthalimideHCID 135800282-(8-Imidazol-1-yl-octyl)-isoindole-1,3-dioneHCID 139528611H-Imidazole-1-octanamine

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 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 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 a like manner from 2-[5-(1H-imidazol-1-yl)pentyl]-1H-isoindole-1,3(2H)-dione was prepared 1H-imidazole-1-pentanamine and from 2-[8-(1H-imidazol-1-yl)octyl]-1H-isoindole-1,3(2H)-dione was prepared 1H-imidazole-1-octanamine.

Workup

  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 a like manner from 2-[5-(1H-imidazol-1-yl)pentyl]-1H-isoindole-1,3(2H)-dione was prepared 1H-imidazole-1-pentanamine

Sources & evidence

ORD record
ord-3fda4de1ae29435ea95f8b254a4d3258
Source dataset
uspto-grants-1986_09
Patent number
US04610981

Reaction notes

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