Potassium Carbonate → tert-butyl 4-(4-phenyl-1H-imidazol-1-yl)piperidine-1-carboxylate

HRID 222246Notes

Reaction equation

HRID 222246 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O.O=[CH:17]C(O)=O.C(=O)([O-])[O-].[K+].[K+].[N+:27]([CH:29]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)S(C1C=CC(C)=CC=1)(=O)=O)#[C-:28]>CN(C=O)C>[C:40]1([C:29]2[N:27]=[CH:28][N:1]([CH:2]3[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]3)[CH:17]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 10967613a-Tosylbenzyl isocyanideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58270814tert-butyl 4-(4-phenyl-1H-imidazol-1-yl)piperidine-1-carboxylateYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of tert-butyl 4-aminopiperidine-1-carboxylate (3.88 g), oxoacetic acid hydrate (1.48 g), and potassium carbonate (4.46 g) in DMF (60 mL) was stirred at room temperature for 3 hours. Then, 1-{[isocyano(phenyl)methyl]sulfonyl}-4-methylbenzene (3.5 g) was added thereto, followed by stirring at room temperature for 14 hours. The solvent was evaporated under reduced pressure, to the residue were added ethyl acetate and water, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate, the combined organic phase was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10) to obtain tert-butyl 4-(4-phenyl-1H-imidazol-1-yl)piperidine-1-carboxylate (3.1 g).

Workup

  1. stirringby stirring at room temperature for 14 hours
  2. customThe solvent was evaporated under reduced pressure, to the residue
  3. additionwere added ethyl acetate and water
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phase was washed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10)

Sources & evidence

ORD record
ord-d4d756b616524d4383cf4fca2dbf34f3
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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