Dimethylformamide → HCID 10112696, compound

HRID 1295775Notes

Reaction equation

HRID 1295775 reaction equation
[CH2:1]([C:5]1[CH:28]=[CH:27][C:8]([C:9]([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)=[O:10])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:29](Br)[CH:30]=[CH2:31].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH2:31]([N:19]1[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:17]([CH:14]2[CH2:15][CH2:16][N:11]([C:9](=[O:10])[C:8]3[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:28][CH:27]=3)[CH2:12][CH2:13]2)[C:18]1=[O:26])[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 16457793HCID 16457793, compound

Product 1

HCID 10112696HCID 10112696, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1-[1-(4-Butyl-benzoyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one (197.2 mg, 0.522 mmol), allyl bromide (260 μL, 3.0 mmol) and cesium carbonate (excess) were added to dimethyl formamide (3 mL) and the suspension was stirred at 120° C. in a sealed tube for 72 hours. The reaction was allowed to cool to room temperature and diluted with water (9 mL) then extracted with ethyl ether (2×10 mL). The combined organic phase was dried over sodium sulfate and purified by column chromatography on silica gel using ethyl ether as the eluent. The product fractions were combined and concentrated to give an oily residue. The residue was triturated with ethyl ether and the white crystals that formed were collected by filtration. Vacuum drying yielded 1-allyl-3-[1-(4-butyl-benzoyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one (144 mg, 66%) as a white crystalline solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionthen extracted with ethyl ether (2×10 mL)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. custompurified by column chromatography on silica gel
  5. concentrationconcentrated
  6. customto give an oily residue
  7. customThe residue was triturated with ethyl ether
  8. customthe white crystals that formed
  9. filtrationwere collected by filtration
  10. customVacuum drying

Sources & evidence

ORD record
ord-44629bab4a564b5a82a557c6b3a634ef
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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