Hydrochloric Acid → 4-(Imidazole-1-yl)butylamine dihydrochloride

HRID 1154333Notes

Reaction equation

HRID 1154333 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.[ClH:24]>C(O)C>[ClH:24].[ClH:24].[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 128033264-(Imidazole-1-yl)butylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.0 g. of N-[4-(1H-imidazol-1-yl)-butyl]isoindole-1,3(2H)-dione, 1.97 ml. of hydrazine hydrate and 100 ml. of ethanol was heated at reflux for 3 hours and then cooled. A 160 ml. of portion of 3N hydrochloric acid was added, the mixture was heated at reflux for one hour and then concentrated. The residue was stirred with 150 ml. of 3N hydrochloric acid and then filtered. The mother liquor was concentrated to dryness, diluted with 10 ml. of ethanol and cooled, giving 1H-imidazole-1-butanamine dihydrochloride (m.p. 132°-146° C.) which was recovered by filtration.

Workup

  1. additionA mixture of 10.0 g
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. temperaturethe mixture was heated
  5. temperatureat reflux for one hour
  6. concentrationconcentrated
  7. filtrationof 3N hydrochloric acid and then filtered
  8. concentrationThe mother liquor was concentrated to dryness
  9. additiondiluted with 10 ml
  10. temperatureof ethanol and cooled

Sources & evidence

ORD record
ord-cc73f243ea6d40c5bbe7536c84b3ee85
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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