Potassium Carbonate → HCID 9889053, compound

HRID 1004303Notes

Reaction equation

HRID 1004303 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15]Br)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:18]=[C:19]1[N:23]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:22]2[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=2[NH:20]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15][N:27]3[CH2:26][CH2:25][CH:24]([N:23]4[C:22]5[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=5[NH:20][C:19]4=[O:18])[CH2:29][CH2:28]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 15428811N-(4-cyclohexyl-phenyl)-2-bromoacetamide

Product 1

HCID 9889053HCID 9889053, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of N-(4-cyclohexyl-phenyl)-2-bromoacetamide (50 mg, 0.17 mmol), 4-(2-keto-1-benzimidazolinyl)-piperidine (41 mg, 0.18 mmol), and potassium carbonate (34 mg, 0.25 mmol) in dimethylsulfoxide (2 mL) was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated to give a yellow oil. The crude oil was purified on reverse phase silica gel column using 100% acetonitrile to give N-(4-cyclohexyl-phenyl)-2-[4-(2-oxo-2,3-dihydrobenzoimidazol-1-yl)-piperidin-1-yl]-acetamide as a yellow solid (21 mg, 30%): mp 130-132° C. 1H NMR (300 MHz, CDCl3) d 9.28 (s, 1 H), 9.05 (s, 1 H), 7.53 (d, 2 H), 7.22 (d, 2 H), 7.11 (m, 4 H), 4.33 (m, 1 H), 3.22 (s, 2 H), 3.12 (d, 2 H), 2.40-2.60 (m, 5 H), 1.70-1.90 (m, 7 H), 1.20-1.60 (m, 5 H). MS m/z 433 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customThe crude oil was purified on reverse phase silica gel column

Sources & evidence

ORD record
ord-8b441b21f02d49b4a19b63a2c921ee8d
Source dataset
uspto-grants-2000_04
Patent number
US06048900

Reaction notes

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