Ammonia → 4-[1-(1H-imidazol-1-yl)ethyl]benzenamine

HRID 1723122Notes

Reaction equation

HRID 1723122 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH3:11])=[CH:6][CH:5]=1)([O-])=O.S1C=CC=C1.N.[H][H]>CO.[Pt]>[N:12]1([CH:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH3:11])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8030ThiopheneHCID 200265621-[1-(4-nitrophenyl)ethyl]-1H-imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 145183654-[1-(1H-imidazol-1-yl)ethyl]benzenamineYield 91.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent3×

Procedure

(a-3) A mixture of 34.4 parts of 1-[1-(4-nitrophenyl)ethyl]-1H-imidazole, 2 parts of a solution of thiophene in methanol 4%, 200 parts of methanol and 200 parts of methanol saturated with ammonia was hydrogenated at normal pressure and at room temperature with 4 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The oily residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane (2:1 by volume). The product was filtered off and dried, yielding 27 parts (91.3%) of 4-[1-(1H-imidazol-1-yl)ethyl]benzenamine; mp. 130° C. (int. 114).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe oily residue was crystallized from a mixture of 2-propanol and 2,2'-oxybispropane (2:1 by volume)
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-6d0827867b28445d92eddd3148483cd2
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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