Hydrochloric Acid → HCID 67587995, compound

HRID 1078378Notes

Reaction equation

HRID 1078378 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=O.[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[C:19]1[CH3:23].[BH4-].[Na+].S(=O)(=O)(O)O.[ClH:31].[CH2:32](O)[CH3:33]>CO.CCOCC>[ClH:31].[ClH:31].[CH3:23][C:19]1[N:18]([CH2:17][CH2:16][CH2:15][NH:14][CH2:1][C:3]2[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([O:11][CH2:32][CH3:33])=[O:10])=[CH:5][CH:4]=2)[CH:22]=[CH:21][N:20]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1118Sulfuric AcidHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 31521053-(2-methyl-1H-imidazol-1-yl)propan-1-amineHCID 4311764Sodium borohydride

Product 1

HCID 67587995HCID 67587995, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Formylcinnamic acid (1.76 g) and 1-(3-aminopropyl)-2-methylimidazole (2.78 g) were stirred in methanol (100 ml) for 5 hours at ambient temperature. Sodium borohydride (1.14 g) was added and the mixture stirred for 2 days at ambient temperature. The reaction mixture was evaporated to dryness. The residue was dissolved in water (60 ml) and washed with dichloromethane. The aqueous solution was neutralised with 5M hydrochloric acid and then washed with dichloromethane. The aqueous layer was evaporated to dryness to give crude 4-[3-(2-methylimidazol-1-yl)propylaminomethyl]cinnamic acid which was boiled under reflux in absolute ethanol (50 ml) and concentrated sulphuric acid (1.5 ml) with stirring for 20 hours. The mixture was hot filtered and the residue dissolved in water, basified with 2M sodium hydroxide and extracted into ethyl acetate to yield an oil which was dissolved in ether and treated with ethereal hydrogen chloride. The solid was collected by filtration and recrystallised from propan-2-ol to give ethyl 4-[3-(2-methylimidazol-1-yl)propylaminomethyl]cinnamate dihydrochloride, m.p. 109°-110.5° C.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in water (60 ml)
  3. washwashed with dichloromethane
  4. washwashed with dichloromethane
  5. customThe aqueous layer was evaporated to dryness
  6. customto give crude 4-[3-(2-methylimidazol-1-yl)propylaminomethyl]cinnamic acid which
  7. filtrationThe mixture was hot filtered
  8. dissolutionthe residue dissolved in water
  9. extractionextracted into ethyl acetate
  10. customto yield an oil which
  11. filtrationThe solid was collected by filtration
  12. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-eb8cbac289a1479688284ef98eaf87cd
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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