Phenacyl bromide → HCID 18536371, compound

HRID 412616Notes

Reaction equation

HRID 412616 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:33]=[CH:32][C:18]([O:19][CH2:20][C:21]3[NH:22][C:23]4[CH:29]=[C:28]([C:30]#[N:31])[CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:36](Br)[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:38]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:33]=[CH:32][C:18]([O:19][CH2:20][C:21]3[N:25]([CH2:36][C:37]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:38])[C:24]4[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:23]=4[N:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 18536444HCID 18536444, compound

Product 1

HCID 18536371HCID 18536371, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)-phenoxymethyl]-5-cyanobenzimidazole (915 mg) in dimethylformamide (15 ml) was added 60% sodium hydride (90 mg) with ice-cooling, and the mixture was stirred at the same temperature for 20 min. Phenacyl bromide (426 mg) was added and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained residue was purified by HPLC (hexane:ethyl acetate=2:3) to give the title compound (385 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. customAfter completion of the reaction
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washwashed successively with water and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by HPLC (hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-a6e1494506c1430d9922a4b98d9fc3c5
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…