Triethylamine → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-carbamoyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 47527Notes

Reaction equation

HRID 47527 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([N:29]([CH2:32]C)CC)C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:36]>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:32](=[O:36])[NH2:29])[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 98872931-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-carbamoyl-1,3-dihydro-2H-benzimidazol-2-oneYield 69.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-[1-(1-Methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (49 mg) and 30 mg of triethylamine were dissolved in 4 ml of chloroform, and to which 30 mg of (4-nitrophenyl) chloroformate was added, followed by 30 minutes' stirring at room temperature. Thereafter the solvent was distilled off, and the resulting residue was dissolved in 5 ml of tetrahydrofuran. To the solution 1 ml of aqueous ammonia was added and stirred for 30 minutes at room temperature. Then water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to provide 38 mg of the title compound as a colorless solid.

Workup

  1. distillationThereafter the solvent was distilled off
  2. dissolutionthe resulting residue was dissolved in 5 ml of tetrahydrofuran
  3. additionTo the solution 1 ml of aqueous ammonia was added
  4. stirringstirred for 30 minutes at room temperature
  5. additionThen water was added to the reaction liquid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-33d360d89b5744b48d6cb5db5891c71d
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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