3-Methoxyaniline → (3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amine

HRID 2043346Notes

Reaction equation

HRID 2043346 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.[BH4-].[Na+]>CO>[N:15]1[CH:16]=[C:12]([CH2:10][NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:13][CH:14]=1

Participants

5

Reactant 3

HCID 108243-MethoxyanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59728243(3H-Imidazol-4-ylmethyl)-(3-methoxy-phenyl)-amineYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of m-anisidine (0.91 ml, 8.12 mmol) in methanol (25 ml) was added 4-formylimidazole (0.86 g, 8.93 mmol). After stirring the mixture overnight at room temperature sodium borohydride (0.46 g, 12.2 mmol) was added. The reaction mixture was then concentrated in vacuo. The residue was purified using flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: methanol/dichloromethane 9:1) to yield a white solid (1.34 g, 18%); MS (ISP): 204.1 ([M+H]+).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customThe residue was purified

Sources & evidence

ORD record
ord-c595360a005d4b628ed5b624a35b0594
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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