Water → (RS)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-one

HRID 1675370Notes

Reaction equation

HRID 1675370 reaction equation
[C:1]1(=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[O:14]=[C:15]1[N:19]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[NH:16]1.[Na].O>O1CCCC1.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH:1]1([N:23]2[CH2:22][CH2:21][CH:20]([N:19]3[C:18]4[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=4[NH:16][C:15]3=[O:14])[CH2:25][CH2:24]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 752291-AcenaphthenoneHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 5360545Sodium

Product 1

HCID 10309214(RS)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-oneYield 18.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Acenaphthen-1-one (1.68 g, 10 mmol) was dissolved in tetrahydrofuran (THF, 15 ml). 4-(2-Keto-1-benzoimidazolinyl)piperidine (2.17 g, 10 mmol) and tetraisopropyl orthotitanate (3.4 g, 12 mmol) were added and the mixture was stirred at room temperature for 20 hr. The solvent was evaporated and a mixed solvent (15 ml) of THF/ethanol (1:2) was added to the obtained residue for dissolution. Sodium cyanoborohydrate (2.1 mmol) was added to this solution, and the mixture was stirred at stirred at room temperature for one day. Water was added, and the precipitate was removed by celite filtration and washed with ethanol. The filtrate was extracted with chloroform and washed with water and saturated brine. The extract was dried over sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.68 g) as yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. additiona mixed solvent (15 ml) of THF/ethanol (1:2) was added to the obtained residue for dissolution
  3. stirringthe mixture was stirred
  4. stirringat stirred at room temperature for one day
  5. customthe precipitate was removed by celite filtration
  6. washwashed with ethanol
  7. extractionThe filtrate was extracted with chloroform
  8. washwashed with water and saturated brine
  9. dry with materialThe extract was dried over sodium sulfate
  10. concentrationconcentrated
  11. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-4bf050a3eda548e396aad680ad59e929
Source dataset
uspto-grants-2011_08
Patent number
US08003669B2

Reaction notes

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