Hydrochloric Acid → 2-phenyl-1H-imidazole-1-propanamine

HRID 1078409Notes

Reaction equation

HRID 1078409 reaction equation
[C:1]1([C:7]2[N:8]([CH2:12][CH2:13][CH2:14][N:15]3C(=O)C4=CC=CC=C4C3=O)[CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>O>[C:1]1([C:7]2[N:8]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:9]=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19429428N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide

Product 1

HCID 135889112-phenyl-1H-imidazole-1-propanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
95 °C

Procedure

A mixture of N-[3-(2-phenylimidazol-1-yl)propyl]phthalimide (17.0 g), sodium hydroxide (1.1 g) and water (5.4 ml) was heated at 95° C. for 48 hours. On cooling, a mixture of concentrated hydrochloric acid (66 ml) and water (13 ml) was added and the mixture boiled under reflux for 6 hours. After standing at ambient temperature for 16 hours, the mixture was filtered and the filtrate evaporated to dryness under reduced pressure. The residue was treated with water (16 ml) then cooled and sodium hydroxide (24 g) added in portions. The solution was extracted with diethyl ether and then with dichloromethane. The combined organic extracts were dried and evaporated to give an oil which was distilled under reduced pressure to give 3-(2-phenylimidazol-1-yl)propylamine, b.p. 128° C. (0.05 mmHg).

Workup

  1. temperatureOn cooling
  2. additionwas added
  3. temperatureunder reflux for 6 hours
  4. filtrationthe mixture was filtered
  5. customthe filtrate evaporated to dryness under reduced pressure
  6. additionThe residue was treated with water (16 ml)
  7. temperaturethen cooled
  8. additionsodium hydroxide (24 g) added in portions
  9. extractionThe solution was extracted with diethyl ether
  10. customThe combined organic extracts were dried
  11. customevaporated
  12. customto give an oil which
  13. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-3dd8946d01f541d5948e0b9871651ef7
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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