Hydrochloride methanol → 6-(Aminomethyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one, hydrochloride

HRID 2108837Notes

Reaction equation

HRID 2108837 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([CH2:11][NH:12]C(=O)OC(C)(C)C)[CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:20].[ClH:21].CO>>[ClH:21].[NH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]2[NH:4][C:3](=[O:20])[N:2]([CH3:1])[C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86609348tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate

Product 1

HCID 1317273876-(Aminomethyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one, hydrochlorideYield 86%

Procedure

A mixture of tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate (658 mg, 2.37 mmol) and 10% hydrogen chloride-MeOH was stirred for 2 hours at ambient temperature. The formed precipitate was collected and washed with DCM to give the title compound as a white solid (436 mg, 86%). 1H NMR (CDCl3): δ 3.28 (3H, s), 3.73 (2H, brs), 7.01 (1H, d, J=7.9 Hz), 7.12 (1H, d, J=7.9 Hz), 7.28 (1H, d, J=8.5 Hz), 8.03-8.67 (3H, m), 11.02 (1H, s). MS (ESI) m/z 176 (M−H)+.

Workup

  1. customThe formed precipitate was collected
  2. washwashed with DCM

Sources & evidence

ORD record
ord-1934d7993f9f4505b0aced347bfbd121
Source dataset
uspto-grants-2009_04
Patent number
US07514457B2

Reaction notes

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