Acetic Acid → 2-Aminoethylbenzimidazole diacetate

HRID 1601067

Reaction equation

HRID 1601067 reaction equation
[C:1]([CH2:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)#[N:2].[CH3:13][C:14]([OH:16])=[O:15]>[Pd]>[C:14]([OH:16])(=[O:15])[CH3:13].[C:14]([OH:16])(=[O:15])[CH3:13].[NH2:2][CH2:1][CH2:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 204551H-Benzimidazole-2-acetonitrile

Product 1

HCID 857400092-Aminoethylbenzimidazole diacetateYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture containing 2-cyanomethylbenzimidazole (2.0 g, 12.7 mmol), 10% Pd/C (1.0 g), and AcOH (40 mL) was hydrogenated at 42 psi for 6 h in a Parr apparatus. The reaction mixture was filtered through a bed of Celite® and concentrated to give the title compound (3.4 g, 95%): 1H NMR (250 MHz, CDCl3) δ 7.04-28.13 (m, 7H), 3.17-3.39 (m, 4H); MS (ES) m/e 162.0 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-90a52a89dc02470caff06ce6db792efc
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Linked notes

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