Triethylamine → (4-benzyloxy-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-amine

HRID 410185Notes

Reaction equation

HRID 410185 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([N:18]([CH2:21][CH3:22])[CH2:19]C)C.C[NH:24][C:25]1C(N)=C[CH:28]=[CH:29][CH:30]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:19]2[N:18]([CH3:16])[C:21]3[CH:22]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 228604-BenzyloxyanilineHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 59327107(4-benzyloxy-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzyloxy-phenylamine (2 g, 8.4 mmol) in 30 mL of DCM was added triethylamine (1 mL) and di-2-pyridylthionocarbonate (2.5 g, 8.4 mmol). The resulting mixture was stirred at RT for 2 h. The reaction mixture was diluted with DCM and washed with water and brine. The organic layer was then dried over Na2SO4, filtered and concentrated. The residue was dissolved in 30 mL DMF, N-methyl-benzene-1,2-diamine (1.5 g, 12.7 mmol) and EDCI (2 g, 10.5 mmol). The resulting mixture was heated at 70° C. for 4 h. The reaction was cooled to RT, diluted with ethyl acetate and washed with water and brine. Purification by silica gel chromatography (98:2 chlorforma/MeOH) afforded the desired product (4-benzyloxy-phenyl)-(1-methyl-1H-benzoimidazol-2-yl)-amine. [M+1]=330.1

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 30 mL DMF
  6. temperatureThe resulting mixture was heated at 70° C. for 4 h
  7. temperatureThe reaction was cooled to RT
  8. washwashed with water and brine
  9. customPurification by silica gel chromatography (98:2 chlorforma/MeOH)

Sources & evidence

ORD record
ord-c14814b60f184b639384d8b731f6453d
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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