p-Toluenesulfonic acid → N-(3-phenylpropyl)-5-imidazol-1-ylpentylamine

HRID 323966Notes

Reaction equation

HRID 323966 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[C:12]1([CH2:18][CH2:19][CH:20]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[C:12]1([CH2:18][CH2:19][CH2:20][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7707BenzenepropanalHCID 4311764Sodium borohydrideHCID 71384341H-Imidazole-1-pentanamine

Product 1

HCID 18349747N-(3-phenylpropyl)-5-imidazol-1-ylpentylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 1-(5-aminopentyl)imidazole (3.48 g), 3-phenylpropionaldehyde (3.08 g), p-toluenesulphonic acid (0.1 g) and toluene (90 ml) was boiled under reflux whilst removing the water formed using a Dean & Stark apparatus under nitrogen for 2 hours. The mixture was evaporated to dryness under reduced pressure to give an oil which was dissolved in IMS (100 ml) and cooled to 5° C. under nitrogen. Sodium borohydride (0.87 g) was added to the solution with stirring. The mixture was allowed to warm to 20° C. and stirred at this temperature for 16 hours. The solvent was removed under reduced pressure. The residue was dissolved in water and acidified to pH 2 with 2M hydrochloric acid. The solution was then basified with 2M sodium hydroxide solution (100 ml) and extracted with ethyl acetate to give an oil. The oil was distilled under high vacuum b.p. 250° C. at 0.04 mbar. The distillate was purified by flash column chromatography on silica using ethyl acetate/methanol/triethylamine (80:10:10) as the mobile phase to give N-(3-phenylpropyl)-5-imidazol-1-ylpentylamine 0.75 hydrate.

Workup

  1. temperatureunder reflux
  2. customwhilst removing the water
  3. customformed
  4. customfor 2 hours
  5. customThe mixture was evaporated to dryness under reduced pressure
  6. customto give an oil which
  7. temperatureto warm to 20° C.
  8. stirringstirred at this temperature for 16 hours
  9. customThe solvent was removed under reduced pressure
  10. dissolutionThe residue was dissolved in water
  11. extractionextracted with ethyl acetate
  12. customto give an oil
  13. distillationThe oil was distilled under high vacuum b.p. 250° C. at 0.04 mbar
  14. distillationThe distillate was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-88e39ab315f64f46b99ea5d0de67dcc1
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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