Potassium Iodide → HCID 86758161, compound

HRID 2186379Notes

Reaction equation

HRID 2186379 reaction equation
Cl.Cl.[O:3]=[C:4]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14]Cl)[CH2:9][C@@H:8]1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[SH:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1>C(#N)C.CO>[O:3]=[C:4]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH2:9][C@@H:8]1[C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 86758162HCID 86758162, compoundHCID 178418616HCID 178418616, compound

Product 1

HCID 86758161HCID 86758161, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1.35 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(2-chloroethyl)piperidine-3-carboxylate dihydrochloride in 20 cm3 of acetonitrile was stirred at a temperature in the region of 20° C. under an inert atmosphere. 1.37 g of potassium carbonate and 0.456 g of potassium iodide were added, followed by 0.367 g of 2-mercaptopyridine and 1 cm3 of methanol. A red suspension was obtained, which suspension was heated at a temperature in the region of 80° C. for 1 hour 30 minutes. After cooling the reaction mass to a temperature in the region of 20° C., the insoluble material was filtered off and washed with acetonitrile. The filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The evaporation residue was purified by chromatography under a nitrogen pressure of 100 kPa on a column of silica gel (particle size 40-63 μm; diameter 3.5 cm; silica height 35 cm), elution was carried out with an ethyl acetate/methanol (95/5 by volume) mixture, and 35-cm3 fractions were collected. Fractions 19 to 40 were combined and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.77 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-ylthio)ethyl]piperidine-3-carboxylate was obtained in the form of a viscous oil with a red color.

Workup

  1. customA red suspension was obtained
  2. temperaturewhich suspension was heated at a temperature in the region of 80° C. for 1 hour 30 minutes
  3. temperatureAfter cooling the reaction mass to a temperature in the region of 20° C.
  4. filtrationthe insoluble material was filtered off
  5. washwashed with acetonitrile
  6. customThe filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  7. customThe evaporation residue was purified by chromatography under a nitrogen pressure of 100 kPa
  8. washon a column of silica gel (particle size 40-63 μm; diameter 3.5 cm; silica height 35 cm), elution
  9. customwere collected
  10. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-04c808709ad1466c84742d35a4663371
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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