Potassium Carbonate → HCID 66683855, compound

HRID 1913885Notes

Reaction equation

HRID 1913885 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.CS(O[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[O:12]=[C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH:3]=2)[NH:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 66683855HCID 66683855, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6-hydroxy-3,4-dihydroquinolin-2(1H)-one (5.0 g), tert-butyl 4-(methanesulfonyloxy)piperidine-1-carboxylate (13 g) and potassium carbonate (5.1 g) in N,N-dimethylformamide (30 mL) was stirred at 100° C. for 20 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with chloroform. The organic layer was washed with brine and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform/hexane=4/1) to give the titled compound (6.9 g, 65%) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform/hexane=4/1)

Sources & evidence

ORD record
ord-943afba652164cb8b32208fe69e4d09d
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

Loading…