Acetyl chloride → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-acetyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 47520Notes

Reaction equation

HRID 47520 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[C:27](Cl)(=[O:29])[CH3:28].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([C:27](=[O:29])[CH3:28])[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 98872321-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-acetyl-1,3-dihydro-2H-benzimidazol-2-oneYield 14.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-[1-(1-Methoxycarbonylpiperidin -4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (32 mg) was dissolved in 5 ml of chloroform and 9 mg of acetyl chloride and 11 mg of triethylamine were added to the solution, followed by one day's stirring at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction liquid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to provide 5.1 mg of the title compound as a colorless oil.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-e8f27e40ffa04542ae3014090b1bfa48
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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