Phosphorus oxychloride → 2-Chloro-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazole

HRID 2235561Notes

Reaction equation

HRID 2235561 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]1[C:14]2[N:15]([CH3:19])[C:16](=O)[NH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:2].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:16]1[N:15]([CH3:19])[C:14]2[C:9]([N:4]3[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]3[CH2:1][CH3:2])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685810967-(2-Ethyl-1-piperidinyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 685813412-Chloro-7-(2-ethyl-1-piperidinyl)-1-methyl-1H-benzimidazoleYield 90%

Procedure

A mixture of 7-(2-ethyl-1-piperidinyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (200 mg, 0.77 mmol) and phosphorus oxychloride (3.55 g, 23.1 mol) was refluxed for 12 h with stirring and concentrated to dryness under vacuum. The residue was purified by column chromatography eluting with a 10% acetone/hexanes mixture to afford 192 mg (90%) of the title compound.

Workup

  1. temperaturewas refluxed for 12 h
  2. concentrationconcentrated to dryness under vacuum
  3. customThe residue was purified by column chromatography
  4. washeluting with a 10% acetone/hexanes mixture

Sources & evidence

ORD record
ord-3dc7d58ba548429f924801fdf1285f1f
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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