4-Bromo-2-methoxy-6-methylaniline → N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazol-2-amine

HRID 2235562Notes

Reaction equation

HRID 2235562 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[CH2:18][CH3:19])=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:20][C:21]1[CH:27]=[C:26]([CH3:28])[C:24]([NH2:25])=[C:23]([O:29][CH3:30])[CH:22]=1>C(OCC)(=O)C>[Br:20][C:21]1[CH:27]=[C:26]([CH3:28])[C:24]([NH:25][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([N:12]4[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]4[CH2:18][CH3:19])=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:23]([O:29][CH3:30])[CH:22]=1

Participants

4

Reactant 2

HCID 106802184-Bromo-2-methoxy-6-methylanilineHCID 685813412-Chloro-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazole

Product 1

HCID 58896452N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazol-2-amineYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazole (100 mg, 0.36 mmol) and 4-bromo-2-methoxy-6-methylaniline (390 mg, 1.8 mmol) was heated at 110° C. for 12 h. The mixture was dissolved in ethyl acetate and washed with saturated sodium bicarbonate in water, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with a 15% acetone/hexanes mixture to afford 49.3 mg (30%) of the title compound.

Workup

  1. washwashed with saturated sodium bicarbonate in water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography
  5. washeluting with a 15% acetone/hexanes mixture

Sources & evidence

ORD record
ord-83f0d8b955794d2b902f749bd4fd511e
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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