1H-Imidazole-1-propanamine → HCID 18349587, compound

HRID 2268259Notes

Reaction equation

HRID 2268259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>CCOCC>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 1425995-Chloro-1-indanone

Product 1

HCID 18349587HCID 18349587, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-chloroindanone (10.2 g, supplied by Lancaster Chemicals) and 1-(3-aminopropyl)imidazole (7.62 g) was heated at 90° C., while bubbling nitrogen through the molten mixture, for 2 hours. The mixture was cooled and dissolved in absolute ethanol (140 ml). Sodium borohydride (4.63 g) was added to the solution and the mixture boiled under reflux for 7 hours. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate to give an oil which was dissolved in ether and filtered. The filtrate was treated with ethereal hydrogen chloride to give a solid which was collected and recrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) (with a charcoal hot filtration) to give N-(5-chloroindan-1-yl)-3-(imidazol-1-yl)propylamine dihydrochloride, m.p. 251-254° C.

Workup

  1. customwhile bubbling nitrogen through the molten mixture
  2. temperatureThe mixture was cooled
  3. dissolutiondissolved in absolute ethanol (140 ml)
  4. additionSodium borohydride (4.63 g) was added to the solution
  5. temperatureunder reflux for 7 hours
  6. customThe solvent was removed under reduced pressure
  7. additionWater was added to the residue
  8. extractionthe mixture was extracted with ethyl acetate
  9. customto give an oil which
  10. filtrationfiltered
  11. additionThe filtrate was treated with ethereal hydrogen chloride
  12. customto give a solid which
  13. customwas collected
  14. customrecrystallised from propan-2-ol/ethanol/water (150 ml/150 ml/trace) (
  15. filtrationwith a charcoal hot filtration)

Sources & evidence

ORD record
ord-024d46f480274538acb262cb47b7b83f
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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