Methyl iodide → 4-(5,6-Dichloro-1-methylbenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamide

HRID 1352666Notes

Reaction equation

HRID 1352666 reaction equation
[Cl:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]2[N:6]=[C:7]([C:9]3[CH:28]=[CH:27][C:12]([C:13]([NH:15][CH:16]4[CH2:21][C:20]([CH3:23])([CH3:22])[N:19]([CH3:24])[C:18]([CH3:26])([CH3:25])[CH2:17]4)=[O:14])=[CH:11][C:10]=3[O:29][CH3:30])[NH:8][C:4]=2[CH:3]=1.[OH-].[K+].I[CH3:37]>CC(C)=O>[Cl:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]2[N:6]([CH3:37])[C:7]([C:9]3[CH:28]=[CH:27][C:12]([C:13]([NH:15][CH:16]4[CH2:21][C:20]([CH3:23])([CH3:22])[N:19]([CH3:24])[C:18]([CH3:25])([CH3:26])[CH2:17]4)=[O:14])=[CH:11][C:10]=3[O:29][CH3:30])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 99134174-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamide

Product 1

HCID 98274274-(5,6-Dichloro-1-methylbenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamideYield 132.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(5,6-dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-methoxybenzamid (0.16 g, 0.33 mmol), prepared as described in Example 4, and KOH (0.0185 g, 0.33 mmol) in acetone (8 ml) was stirred for 1 h at room temperature. Iodomethane (0.047 g, 0.033 mmol) was added and stirring was continued for 24 h. Solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. the organic layer was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by column chromatography eluting with CH2Cl2/MeOH/NH4OH 95:5:0.2. Fraction containing the desired product were collected, evaporated to dryness under reduced pressure and the solid was triturated with diisopropyl ether to give 0.022 g of the title compound (yield 13%), mp=178–180° C.

Workup

  1. customprepared
  2. stirringstirring
  3. waitwas continued for 24 h
  4. customSolvent was removed under reduced pressure
  5. customthe residue was partitioned between water and ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified by column chromatography
  11. washeluting with CH2Cl2/MeOH/NH4OH 95:5:0.2
  12. additionFraction containing the desired product
  13. customwere collected
  14. customevaporated to dryness under reduced pressure
  15. customthe solid was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-8ccd9bf35a4a4e969bc76f987dfd66e5
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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