Potassium Carbonate → 1-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine

HRID 609788Notes

Reaction equation

HRID 609788 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS([CH2:29][CH2:30][O:31][CH2:32][CH:33]=[CH2:34])(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.ClCCl>CC(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:16]2[N:17]([CH2:29][CH2:30][O:31][CH2:32][CH:33]=[CH2:34])[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidineHCID 21226138Dichloromethane ethylacetateHCID 57200585Allyl methanesulfonylethyl ether

Product 1

HCID 183332581-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (1.87 g, 5.68 mmol), allyl methanesulfonylethyl ether (1.83 g, 10.1 mmol), and potassium carbonate (1.60 g, 11.5 mmol) in acetone (21 mL) and water (7 mL). Heat to reflux. After 18 hours, concentrate the reaction mixture in vacuo to remove most of the acetone. Partition the concentrated reaction mixture between ethyl acetate and water. Separate the aqueous layer and extract three times with ethyl acetate. Extract the combined organic layers with saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to to obtain a residue. Chromatograph the residue on silica gel eluting with 15% ethyl acetate/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine: Rf =0.48 (silica gel, 20% ethyl acetate/dichloromethane).

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto remove most of the acetone
  4. customPartition
  5. customthe concentrated reaction mixture between ethyl acetate and water
  6. customSeparate the aqueous layer
  7. extractionextract three times with ethyl acetate
  8. extractionExtract the combined organic layers with saturated aqueous sodium chloride solution
  9. dry with materialDry the organic layer over Na2SO4
  10. filtrationfilter
  11. customevaporate in vacuo
  12. customto to obtain a residue

Sources & evidence

ORD record
ord-15d2865b37b04d78b5cfa6ca2b0cf14e
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

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