2-(Aminomethyl)aniline → 2-Aminobenzimidazole

HRID 1243671Notes

Reaction equation

HRID 1243671 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1CN.Cl[C:11]1[NH:12]C2C=C(OC)C=CC=2[N:15]=1>C(Cl)Cl>[N:1]1[C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[NH:12][C:11]=1[NH2:15]

Participants

4

Reactant 2

HCID 1780962-(Aminomethyl)anilineHCID 5191972-Chloro-5-methoxy-1H-benzimidazole

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-aminobenzylamine (500 mg, 4.1 mmol) and 2-chloro-5-methoxybenzoimidazole (210 mg, 1.2 mmol) was heated at 120° C. for 18 h. The resulting oily residue was dissolved in CH2Cl2 (30 mL) and washed with H2O (30 mL). The organic layer was separated, dried over Na2SO4, and concentrated to provide crude benzimidazole amine as a solid which was treated with CDI (1.0 g, 6.0 mmol) in anhydrous DMF (15 mL). After stirring at RT for 18 h, the reaction mixture was concentrated. The residue was purified by prep TLC to give an oil which was triturated from CH2Cl2 and hexane to yield a solid. Further purification by prep HPLC provided the title compound as white solid. MS m/z: 295 (M+H+); MALDI FTMS (DHB) m/z: 295.1184 (M+H; Calc'd for C16H15N4O2, 295.1189).

Workup

  1. washwashed with H2O (30 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-796975181ffe403c8be2214a460756bf
Source dataset
uspto-grants-2006_10
Patent number
US07119111B2

Reaction notes

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